Photochromic articles that activate behind ultraviolet radiation blocking transparencies and methods for preparation

ABSTRACT

Described are photochromic articles that include a substrate and at least one photochromic material adapted to change from an unactivated state to an activated state by exposure to radiation substantially in a wavelength range from 380 to 410 nanometers (nm) when measured over a wavelength range of from 380 to 700 nm. The photochromic articles demonstrate a photochromic response when activated behind an ultraviolet blocking transparency such as an automotive windshield. For example, the photochromic articles retain at least 12 percent of the activation measured as change in optical density or delta OD under outdoor simulating conditions in the Outdoor Test when tested under conditions simulating an eyeglass wearer behind an automotive windshield in the Behind the Windshield Test. Methods for producing the aforedescribed photochromic articles are also described.

BACKGROUND OF THE INVENTION

[0001] The present invention relates to novel photochromic articles thatactivate or become darker behind an ultraviolet radiation blockingtransparency, e.g., an automotive windshield. More particularly, thisinvention relates to photochromic articles that demonstrate activatedcoloration or darkness when tested under conditions simulating aneyeglass wearer behind an automotive windshield and at least 70 percenttransmittance in the unactivated stated.

[0002] Photochromism is a phenomenon involving a light inducedreversible change in color. An article containing such a material thatbecomes colored upon exposure to light radiation containing ultravioletrays will revert to the original color when the influence of theultraviolet radiation is discontinued. Sources of light radiation thatcontain ultraviolet rays include, for example, sunlight and the light ofa mercury lamp. Discontinuation of the ultraviolet radiation can beachieved for example by storing the photochromic material or article inthe dark or by removing the source of ultraviolet radiation, e.g., bymeans of filtering.

[0003] Typical photochromic articles do not activate or demonstratenegligible activation behind automotive windshields due to the limitedultraviolet radiation available for activation. A photochromic articlethat has been disclosed to function behind such ultraviolet radiationblocking transparencies includes photochromic compounds that activate bymeans of light in the visible spectrum. Such an article requires thepresence of ultraviolet light absorbers to prevent the article frombecoming too dark when not behind the windshield. The unactivated stateof such an article is colored resulting in a percent transmission lessthan 70 percent.

[0004] The present invention provides a photochromic article thatactivates behind ultraviolet radiation blocking transparencies and amethod for preparing such articles using photochromic materials thathave been adapted to change from an unactivated form to an activatedform by exposure to activating radiation substantially in the range offrom 380 to 410 nanometers (nm), when such activating radiation ismeasured over a range from 380 to 700 nm.

BRIEF DESCRIPTION OF THE FIGURE

[0005]FIG. 1 shows the spectrum of the light passing through theautomotive windshield simulating system used in the Behind theWindshield Test described herein in Example 13.

DETAILED DESCRIPTION OF THE INVENTION

[0006] It is noted that, as used in this specification and the appendedclaims, the singular forms “a,” “an,” and “the” include plural referentsunless expressly and unequivocally limited to one referent.

[0007] For the purposes of this specification, unless otherwiseindicated, all numbers expressing quantities of ingredients, reactionconditions, and other parameters used in the specification and claimsare to be understood as being modified in all instances by the term“about”. Accordingly, unless indicated to the contrary, the numericalparameters set forth in the following specification and attached claimsare approximations that may vary depending upon the desired propertiessought to be obtained by the present invention. At the very least, andnot as an attempt to limit the application of the doctrine ofequivalents to the scope of the claims, each numerical parameter shouldat least be construed in light of the number of reported significantdigits and by applying ordinary rounding techniques.

[0008] Notwithstanding that the numerical ranges and parameters settingforth the broad scope of the invention are approximations, the numericalvalues set forth in the specific examples are reported as precisely aspossible. Any numerical value, however, inherently contain certainerrors necessarily resulting from the standard deviation found in theirrespective testing measurements.

[0009] The phrase “an at least partial coating” means an amount ofcoating covering from a portion to the complete surface of thesubstrate. The phrase “an at least partially cured coating” refers to acoating in which the curable or cross-linkable components are from atleast partially cured up to fully cured, crosslinked and/or reacted. Inalternate non-limiting embodiments of the present invention, the degreeof reacted components can vary widely, e.g., from 5% to 100% of all thepossible curable, crosslinkable and/or reactable components.

[0010] The phrase “an at least partially abrasion resistant coating orfilm” refers to a coating or film that demonstrates a resistance toabrasion that is greater than the standard reference material, typicallya plastic made of CR-39® monomer available from PPG Industries, Inc, astested in a method comparable to ASTM F-735 Standard Test Method forAbrasion Resistance of Transparent Plastics and Coatings Using theOscillating Sand Method. The phrase “an at least partiallyantireflective coating” is a coating that at least partially improvesthe antireflective nature of the surface to which it is applied byincreasing the percent transmittance as compared to an uncoated surface.The improvement in percent transmittance can range from 1 to 9 percentabove the uncoated surface. Put another way, the percent transmittanceof the coated surface can range from a percentage greater than theuncoated surface up to 99.9.

[0011] In one non-limiting embodiment, the use of at least onephotochromic material adapted to change from an unactivated form to anactivated form by exposure to activating radiation substantially in thewavelength range of from 380 to 410 nm in a photochromic article testedin the Behind the Windshield Test adapts the photochromic article toretain at least 12 percent of the coloration, measured as delta OD orΔOD, that would have occurred if the adapted photochromic article wasactivated under conditions simulating outdoor exposure as described inthe Outdoor Test in Example 13 herein.

[0012] In another non-limiting embodiment, the adapted photochromicarticle retains at least 20 percent of the coloration. In a furthernon-limiting embodiment, the adapted photochromic article retains atleast 25 percent of the coloration exhibited in the Outdoor Test whentested in the Behind the Windshield Test. The coloration or percent ΔODretained by the adapted photochromic article of the present inventioncan range between any combination of these values, inclusive of therecited range, e.g., from 12 to 100 percent, or from 20 to 90 percent orfrom 25 to 50 percent.

[0013] In an alternate non-limiting embodiment, the photochromic articleof the present invention is adapted to exhibit an unactivated stateluminous transmittance of greater than 70 percent at 23° C., anactivated state luminous transmittance at saturation less than 30percent when activated at 23° C. by simulated sunlight from a xenon arclamp set at 6.7 Watts/meter² UVA and 50,000 lumens/meter², and anactivated state luminous transmittance at saturation less than 60percent when activated at 28° C. by simulated sunlight from a xenon arclamp through an UV blocking transparency rendering an irradianceintegrated between 380 and 420 nanometers of 0.75 Watts/meter² and 1,700lumens/meter².

[0014] In another non-limiting embodiment, the photochromic article ofthe present invention is adapted to exhibit an unactivated stateluminous transmittance of greater than 80 percent at 23° C., anactivated state luminous transmittance at saturation less than 30percent when activated at 23° C. by simulated sunlight from a xenon arclamp set at 6.7 Watts/meter² UVA and 50,000 lumens/meter², and anactivated state luminous transmittance at saturation less than 40percent when activated at 28° C. by simulated sunlight from a xenon arclamp through an UV blocking transparency rendering an irradianceintegrated between 380 and 420 nanometers of 0.75 Watts/meter² and 1,700lumens/meter².

[0015] In the aforementioned alternate non-limiting embodiment, thephotochromic articles reach saturation within 15 to 30 minutes ofexposure to the simulated sunlight and/or simulated sunlight filtered bythe UV radiation blocking transparency at 23° C. and 28° C. The term“activated luminous state transmittance at saturation” means that thetransmittance of the photochromic article has reached a point where itwill not substantially change due to continued exposure to simulatedsunlight. Stated another way, the transmittance at saturation uponcontinued exposure to activating radiation does not vary by more than 5percent of the percent transmittance value.

[0016] The aforementioned unactivated state luminous transmittance at23° C. can range between any of the aforestated values, e.g., from 70.1to 100 percent or from 80.1 to 100 percent, and their inclusive values,e.g., from 71 to 99 percent or from 81 to 99 percent. The activatedstate luminous transmittance at saturation when the photochromic articleis activated at 23° C. by simulated sunlight from a xenon arc lamp setat 6.7 Watts/meter² UVA and 50,000 lumens/meter² can range between theaforestated values, e.g., from 29.9 to 0 percent, and their inclusivevalues, e.g., from 29 to 10 percent, or from 25 to 15 percent. Theactivated state luminous transmittance at saturation when thephotochromic article is activated at 28° C. by simulated sunlight from axenon arc lamp through an UV blocking transparency rendering anirradiance integrated between 380 and 420 nanometers of 0.75Watts/meter² and 1,700 lumens/meter². can range between any of theaforestated values, e.g., from 0 to less than 60 percent, e.g., 59.9percent, or from 0 to less than 40 percent e.g., 39.9 percent, and theirinclusive values, e.g., from 1 to 59 percent, or from 10 to 50 percentor from 15 to 40 percent.

[0017] The photochromic materials used to adapt the photochromic articlefor activation behind ultraviolet radiation blocking transparencies arereferred to herein as Behind the Windshield photochromic materials orBWS photochromic materials.

[0018] The Behind the Windshield Test and the Outdoor Test are describedin Example 13 herein. Basically, test samples containing BWSphotochromic materials with or without other photochromic materials aretested for photochromic response, e.g., the change in optical density,with the simulated windshield in place under conditions simulating aneyeglass wearer behind an automotive windshield exposure (BWS) versusconditions simulating outdoor exposure in the Outdoor Test (OS). Theretained optical density is calculated by using the following formula:

% ΔOD Retained=100×(ΔOD _(BWS) /ΔOD _(OS)).

[0019] In one non-limiting embodiment, the photochromic articles of thepresent invention are substantially free of ultraviolet absorbingmaterials in concentrations that would substantially inhibit theactivation of the photochromic materials by radiation below 380nanometers. In an alternate non-limiting embodiment, the photochromicarticles of the present invention do not contain ultraviolet absorbingmaterials in concentrations that would prevent greater than 50 percentof the activation of the photochromic materials, as measured by delta ODby radiation below 380 nanometers.

[0020] In a series of non-limiting embodiments, the BWS photochromicmaterials of the present invention include photochromic materialsadapted to change from an unactivated form to an activated form byexposure to radiation substantially in the wavelength range from 380 to410 nanometers when measured over a range of from 380 to 700 nanometers.Classes of photochromic materials that can include BWS photochromicmaterials include naphthopyrans, benzopyrans, phenanthropyrans,indenonaphthopyrans, oxazines, metal-dithiozonates, fulgides,fulgimides, spiro(indoline)pyrans or mixtures thereof. In onenon-limiting embodiment, the BWS materials are chosen from the followingphotochromic materials and mixtures thereof. In the definitions of thesubstituents shown in formulae I to XIV, like symbols have the samemeaning unless stated otherwise.

[0021] In one non-limiting embodiment, a photochromic material is chosenfrom a fluoranthenoxazine represented by the following graphic formulaI:

[0022] wherein,

[0023] (a) R₁ is chosen from hydrogen, C₁-C₈ alkyl, C₃-C₇ cycloalkyl,phen(C₁-C₄)alkyl, naphth(C₁-C₄)alkyl, allyl, acrylyloxy(C₂-C₆)alkyl,methacrylyloxy(C₂-C₆)alkyl, C₂-C₄acyloxy (C₂-C₆)alkyl,carboxy(C₂-C₆)alkyl, cyano(C₂-C₆)alkyl, hydroxy(C₂-C₆)alkyl,triarylsilyl, triarylsilyloxy, tri(C₁-C₆)alkylsilyl,tri(C₁-C₆)alkylsilyloxy, tri(C₁-C₆)alkoxysilyl,tri(C₁-C₆)alkoxysilyloxy, di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyl,di(C₁-C₆)alkyl(C₁-C₆alkoxy)silyloxy, di(C₁-C₆)alkoxy(C₁-C₆alkyl)silyl,di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyloxy, C₁-C₆ alkoxy(C₂-C₄)alkyl or(C₂H₄O)_(r).CH₃, wherein r is an integer from 1 to 6;

[0024] (b) R₂ is chosen from C₁-C₅ alkyl, C₁-C₅ alkoxy, nitro, cyano,C₁-C₈ alkoxycarbonyl, C₁-C₄ acyloxy, halo, C₁-C₄ monohaloalkyl or C₁-C₄polyhaloalkyl; said halo substituents being chloro, fluoro, iodo orbromo and q is 0, 1 or 2;

[0025] (c) R₃ and R₄ are each independently chosen from C₁-C₅ alkyl,benzyl, phenyl, mono- or di-substituted phenyl, said phenyl substituentsbeing C₁-C₅ alkyl or C₁-C₅ alkoxy; or R₃ and R₄ taken together form agroup chosen from a cyclic ring of from 5 to 8 carbon atoms whichincludes the spiro carbon atom; examples of such groups includenorbornyl or adamantyl;

[0026] (d) R₅ is chosen from hydrogen, —CH₂Q and —C(O)W, wherein Q ishalogen, hydroxy, benzoyloxy, C₁-C₆ alkoxy, triarylsilyl,triarylsilyloxy, tri(C₁-C₆)alkylsilyl, tri(C₁-C₆)alkylsilyloxy,tri(C₁-C₆)alkoxysilyl, tri(C₁-C₆)alkoxysilyloxy, di(C₁-C₆)alkyl(C₁-C₆alkoxy)silyl, di(C₁-C₆)alkyl(C_(l)-C₆ alkoxy)silyloxy,di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyl, di(C₁-C₆)alkoxy(C_(l)-C₆alkyl)silyloxy, C₂-C₆ acyloxy, amino, C₁-C₆ mono-alkylamino, C₁-C₆dialkylamino, morpholino, piperidino, 1-indolinyl, pyrrolidyl, or thegroup, —OCH(R₈)Z; W is the group, —OCH(R₈)Z, or an unsubstituted,mono-substituted, or di-substituted heterocyclic ring containing 5 to 6ring atoms, which ring includes as the hetero atom a nitrogen atom aloneor one additional hetero atom of nitrogen or oxygen; examples of suchheterocyclic rings include 1-indolinyl, morpholino, piperidino,1-pyrrolidyl, 1-imidazolidyl, 2-imidazolin-1-yl, pyrazolidyl,pyrazolinyl or 1-piperazinyl; wherein Z is —CN, —CF₃, halogen, —C(O)R₈,or —COOR₈, R₈ is hydrogen or C₁-C₆ alkyl; said heterocyclic ringsubstituents being chosen from C₁-C₆ alkyl or C₁-C₆ alkoxy; or W is —OR₉or —N(R₁₀)R₁₁, wherein R₉ is chosen from hydrogen, allyl, C₁-C₆ alkyl,phenyl, mono(C₁-C₆)alkyl substituted phenyl,mono(C₁-C₆)alkoxy-substituted phenyl, phenyl(C₁-C₃)alkyl,mono(C₁-C₆)alkyl substituted phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxysubstituted phenyl(C₁-C₃)alkyl, C₁-C₆ alkoxy(C₂-C₄)alkyl, or C₁-C₆haloalkyl; and R₁₀ and R₁₁ are each independently chosen from hydrogen,C₁-C₆ alkyl, C₅-C₇ cycloalkyl, phenyl, mono- or di-substituted phenyl,or R₁₀ and R₁₁ together with the nitrogen atom form a mono- ordi-substituted or unsubstituted heterocyclic ring containing from 5 to 6ring atoms, which ring includes as the hetero atom said nitrogen atomalone or one additional hetero atom of nitrogen or oxygen, said phenyland heterocyclic ring substituents being C₁-C₆ alkyl or C₁-C₆ alkoxy,and each of said halogen or halo groups in this part (d) being fluoro orchloro;

[0027] (e) each R₆ and R₇ is independently chosen for each occurrencefrom aryl, mono(C₁-C₆)alkoxyaryl, di(C₁-C₆)alkoxyaryl,mono(C₁-C₆)alkylaryl, di(C₁-C₆)alkylaryl, bromoaryl, chloroaryl,fluoroaryl, C₃-C₇ cycloalkylaryl, C₃-C₇ cycloalkyl, C₃-C₇ cycloalkyloxy,C₃-C₇ cycloalkyloxy(C₁-C₆)alkyl, C₃-C₇ cycloalkyloxy(C₁-C₆)alkoxy,aryl(C₁-C₆)alkyl, aryl(C₁-C₆)alkoxy, aryloxy, aryloxy(C₁-C₆)alkyl,aryloxy(C₁-C₆)alkoxy, mono- or di(C₁-C₆)alkylaryl(C₁-C₆)alkyl, mono- ordi(C₁-C₆)alkoxyaryl(C₁-C₆)alkyl, mono- ordi(C₁-C₆)alkylaryl(C₁-C₆)alkoxy, mono- ordi(C₁-C₆)alkoxyaryl(C₁-C₆)alkoxy, amino, mono(C₁-C₆)alkylamino,di(C₁-C₆)alkylamino, diarylamino, N-(C₁-C₆)alkylpiperazino,N-arylpiperazino, aziridino, indolino, piperidino, arylpiperidino,morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino,pyrryl, C₁-C₆ alkyl, C₁-C₆ bromoalkyl, C₁-C₆ chloroalkyl, C₁-C₆fluoroalkyl, C₁-C₆ alkoxy, mono(C₁-C₆)alkoxy(C₁-C₄)alkyl, acryloxy,methacryloxy, bromo, chloro or fluoro; and q is independently chosen foreach occurrence form the integer 0, 1, or 2.

[0028] In another non-limiting embodiment, the fluoranthenoxazine isrepresented by graphic formula I wherein:

[0029] (a) R₁ is chosen from C₁-C₈ alkyl, phen(C₁-C₄)alkyl,acrylyloxy(C₂-C₆)alkyl, methacrylyloxy(C₂-C₆)alkyl, carboxy(C₂-C₆)alkyl,tri(C₁-C₆)alkylsilyl, tri(C₁-C₆)alkylsilyloxy, tri(C₁-C₆)alkoxysilyl,tri(C₁-C₆)alkoxysilyloxy, di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyl,di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyloxy, di(C₁-C₆)alkoxy(C₁-C₆alkyl)silylor di(C₁-C₆)alkoxy(C₁-C₆alkyl)silyloxy;

[0030] (b) R₂ is chosen from C₁-C₅ alkyl, C₁-C₅ alkoxy, C₁-C₈alkoxycarbonyl, C₁-C₄ acyloxy, halo, C₁-C₄ monohaloalkyl or C₁-C₄polyhaloalkyl; said halo substituents being chloro or fluoro, and q is0, 1 or 2;

[0031] (c) R₃ and R₄ are each independently chosen from C₁-C₅ alkyl,phenyl; or R₃ and R₄ taken together form a group chosen from a cyclicring of from 5 to 8 carbon atoms which includes the spiro carbon atom;;

[0032] (d) R₅ is chosen from —CH₂Q and —C(O)W, wherein Q is halogen,hydroxy, C₁-C₆ alkoxy, tri(C₁-C₆)alkylsilyl, tri(C₁-C₆)alkylsilyloxy,tri(C₁-C₆)alkoxysilyl, tri(C₁-C₆)alkoxysilyloxy, di(C₁-C₆)alkyl(C₁-C₆alkoxy)silyl, di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyloxy,di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyl, di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyloxyor the group, —OCH(R₈)Z; W is the group, —OCH(R₈)Z, morpholino orpiperidino; Z is —COOR₈, R₈ is C₁-C₆ alkyl; or W is —OR₉ or —N(R₁₀)R₁₁,wherein R₉ is chosen from C₁-C₆ alkyl or phenyl; and R₁₀ and R₁₁ areeach independently chosen from hydrogen, C₁-C₆ alkyl, or R₁₀ and R₁₁together with the nitrogen atom form a heterocyclic ring chosen frommorpholino or piperidino; and each of said halogen or halo groups inthis part (d) being fluoro or chloro;

[0033] (e) each R₆ and R₇ is independently chosen for each occurrencefrom aryl, mono(C₁-C₆)alkoxyaryl, di(C₁-C₆)alkylamino, piperidino,morpholino, C₁-C₆ alkoxy, or fluoro; and q is independently chosen foreach occurrence form the integer 0, 1, or 2.

[0034] In a further non-limiting embodiment, the fluoranthenoxazinerepresented by graphic formula I is chosen from:

[0035] (a)1,3,3-trimethyl-spiro[indoline-2,5′-[3H]-fluorantheno[3,2-b][1,4]oxazine];

[0036] (b) 1,3,3,4,5 (or1,3,3,5,6)-pentamethyl-spiro[indoline-2,5′-[3H]-fluorantheno[3,2-b][1,4]oxazine];

[0037] (c) 1-propyl-3,3,4,5 (or3,3,5,6)-tetramethyl-spiro[indoline-2,5′-[3H]-fluorantheno[3,2-b][1,4]oxazine];

[0038] (d)1-methoxyethyl-3,3-dimethyl-spiro[indoline-2,5′-[3H]-fluorantheno[3,2-b][1,4]oxazine];or

[0039] (e) mixtures thereof.

[0040] The materials represented by graphic formula I can be produced bymethods known to those skilled in the art, for example, as disclosed inU.S. Pat. No. 5,808,063

[0041] In one non-limiting embodiment, a photochromic material is chosenfrom a naphthopyran represented by the following graphic formula II:

[0042] wherein:

[0043] (a) R₁₂ is hydrogen or a C₁-C₆ alkyl;

[0044] (b) R₁₃ is hydrogen or the group, —C(O)J, J being —OR₁₅ or—N(R₁₀)R₁₁, wherein R₁₅ is hydrogen, allyl, C₁-C₆ alkyl, phenyl, C₁-C₆monoalkyl substituted phenyl, C₁-C₆ monoalkoxy substituted phenyl,phenyl(C₁-C₃)alkyl, C₁-C₆ monoalkyl substituted phenyl(C₁-C₃)alkyl,C₁-C₆ monoalkoxy substituted phenyl(C₁-C₃)alkyl, C₁-C₆alkoxy(C₂-C₄)alkyl, or C₁-C₆ monohaloalkyl, and wherein R₁₀ and R₁₁ arethe same as described hereinbefore in (d) for the material representedby graphic formula I, and said halo substituent being chloro or fluoro;

[0045] (c) R₁₄ is —OR₉, —N(R₁₀)R₁₁, wherein R₉, R₁₀ and R₁₁ are the sameas described hereinbefore in (d) for the material represented by graphicformula I, or the group, —C(O)V; wherein V is C₁-C₆ alkyl, phenyl, C₁-C₆mono- or C₁-C₆ di-alkyl substituted phenyl, C₁-C₆ mono- or C₁-C₆di-alkoxy substituted phenyl, C₁-C₆ alkoxy, phenoxy, C₁-C₆ mono- orC₁-C₆ di-alkyl substituted phenoxy, C₁-C₆ mono- or C₁-C₆ di-alkoxysubstituted phenoxy, C₁-C₆ alkylamino, phenylamino, C₁-C₆ mono- or C₁-C₆di-alkyl substituted phenylamino, or C₁-C₆ mono- or C₁-C₆ di-alkoxysubstituted phenylamino, and said halo substituent being chloro, fluoroor bromo, provided that either R₁₂ or R₁₃ is hydrogen; and

[0046] (d) B and B′ are each independently chosen from:

[0047] (i) mono-T-substituted phenyl, wherein the group T is representedby the formula:

—G[(OC₂H₄)_(x)(OC₃H₆)_(y)(OC₄H₈)_(z)]G′—[(OC₂H₄)_(x)(OC₃H₆)_(y)(OC₄H₈)_(z)]G′

[0048] wherein —G being chosen from —C(O)— or —CH₂—, G′ being chosenfrom C₁-C₃ alkoxy or a polymerizable group, x, y and z each beingindependently chosen from a number between 0 and 50, and the sum of x, yand z being between 2 and 50;

[0049] (ii) an unsubstituted, mono-, di-, or tri-substituted aryl group,phenyl or naphthyl;

[0050] (iii) 9-julolidinyl or the unsubstituted, mono- or di-substitutedheteroaromatic group chosen from pyridyl furanyl, benzofuran-2-yl,benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl,dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl orfluorenyl, each of said aryl and heteroaromatic substituents in (ii) and(iii) being independently chosen from hydroxy, —C(O)U, wherein U beinghydroxy, C₁-C₆ alkyl, C₁-C₆ alkoxy, phenyl, mono-substituted phenyl,amino, mono (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, morpholino,piperidino or pyrrolidyl; aryl, mono(C₁-C₆)alkoxyaryl,di(C₁-C₆)alkoxyaryl, mono(C₁-C₆)alkylaryl, di(C₁-C₆)alkylaryl,chloroaryl, fluoroaryl, C₃-C₇ cycloalkylaryl, C₃-C₇ cycloalkyl, C₃-C₇cycloalkyloxy, C₃-C₇ cycloalkyloxy(C₁-C₆)alkyl, C₃-C₇cycloalkyloxy(C₁-C₆)alkoxy, aryl(C₁-C₆)alkyl, aryl(C₁-C₆)alkoxy,aryloxy, aryloxy(C₁-C₆)alkyl, aryloxy(C₁-C₆)alkoxy, mono- ordi(C₁-C₆)alkylaryl(C₁-C₆)alkyl, mono- ordi(C₁-C₆)alkoxyaryl(C₁-C₆)alkyl, mono- ordi(C₁-C₆)alkylaryl(C₁-C₆)alkoxy, mono- ordi(C₁-C₆)alkoxyaryl(C₁-C₆)alkoxy, amino, mono(C₁-C₆)alkylamino,di(C₁-C₆)alkylamino, diarylamino, piperazino, N-(C₁-C₆)alkylpiperazino,N-arylpiperazino, aziridino, indolino, piperidino, morpholino,thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl,C₁-C₆ alkyl, C₁-C₆ chloroalkyl, C₁-C₆ fluoroalkyl, C₁-C₆ alkoxy,mono(C₁-C₆)alkoxy(C₁-C₄)alkyl, acryloxy, methacryloxy, bromo, chloro orfluoro, said aryl being chosen from phenyl or naphthyl;

[0051] (iv) an unsubstituted or mono-substituted group chosen frompyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolinyl,phenothiazinyl, phenoxazinyl, phenazinyl or acridinyl, each of saidsubstituents being independently chosen from C₁-C₆ alkyl, C₁-C₆ alkoxy,phenyl, fluoro, chloro or bromo;

[0052] (v) a monosubstituted phenyl, said phenyl having a substituentlocated at the para position being a linking group, —(CH₂)_(r)— or—O—(CH₂)_(r)—, connected to an aryl group which is a member of anotherphotochromic material, and r being chosen from the integer 1, 2, 3, 4, 5or 6;

[0053] (vi) a group represented by one of the following graphicformulae:

[0054] wherein A being independently chosen in each formula frommethylene or oxygen and D being independently chosen in each formulafrom oxygen or substituted nitrogen, provided that when D is substitutednitrogen, A is methylene; said nitrogen substituents being chosen fromhydrogen, C₁-C₆ alkyl, or C₂-C₆ acyl; each R₂₀ being independentlychosen for each occurrence in each formula from C₁-C₆ alkyl, C₁-C₆alkoxy, hydroxy, chloro or fluoro; R₁₈ and R₁₉ each being independentlychosen in each formula from hydrogen or C₁-C₆ alkyl; and q being chosenfrom the integer 0, 1 or 2;

[0055] (vii) C₁-C₆ alkyl, C₁-C₆ chloroalkyl, C₁-C₆ fluoroalkyl, C₁-C₆alkoxy(C₁-C₄)alkyl, C₃-C₆ cycloalkyl,mono(C₁-C₆)alkoxy(C₃-C₆)cycloalkyl, mono(C₁-C₆)alkyl(C₃-C₆)-cycloalkyl,chloro(C₃-C₆)cycloalkyl, fluoro(C₃-C₆)cyclo-alkyl or C₄-C₁₂bicycloalkyl;

[0056] (viii) a group represented by the following graphic formula:

[0057] wherein L being chosen from hydrogen or C₁-C₄ alkyl and M beingchosen from an unsubstituted, mono-, or di-substituted group chosen fromnaphthyl, phenyl, furanyl, or thienyl; each of said group substituentsbeing independently chosen from C₁-C₄ alkyl, C₁-C₄ alkoxy, fluoro, orchloro; or

[0058] (ix) B and B′ taken together form fluoren-9-ylidene, mono-, ordi-substituted fluoren-9-ylidene or a group being independently chosenfrom saturated C₃-C₁₂ spiro-monocyclic hydrocarbon rings, saturatedC₇-C₁₂ spiro-bicyclic hydrocarbon rings or saturated C₇-C₁₂spiro-tricyclic hydrocarbon rings; each of said fluoren-9-ylidenesubstituents being independently chosen from C₁-C₄ alkyl, C₁-C₄ alkoxy,fluoro or chloro.

[0059] In one non-limiting embodiment, when the T group is a substituenton the photochromic materials as hereinbefore in (d) (i), polymerizationof the photochromic polymerizable compounds can occur by mechanismsdescribed in the definition of “polymerization” in Hawley's CondensedChemical Dictionary, Thirteenth Edition, 1997, John Wiley & Sons, pages901-902. Those mechanisms include by “addition”, in which free radicalsare the initiating agents that react with the double bond of the monomerby adding to it on one side at the same time producing a new freeelectron on the other side, by “condensation”, involving the splittingout of water molecules by two reacting monomers and by so-called“oxidative coupling”. Non-limiting examples of the polymerizable groupsare hydroxy, (meth)acryloxy, 2-(methacryloxy)ethylcarbamyl, or epoxy,e.g., oxiranylmethyl. When there are 2 or more polymerizable groups onthe naphthopyran, they may be the same or different.

[0060] The group, —(OC₂H₄)_(x)—, in the group T formulae, can representpoly(ethylene oxide); —(OC₃H₆)_(y)—, can represent poly(propyleneoxide); and, (OC₄H₈)_(z)—, can represent poly(butylene oxide). When usedin combination, the poly(ethylene oxide), poly(propylene oxide) andpoly(butylene oxide) groups of T can be in a random or block orderwithin the T moiety. The letters x, y and z are each a number between 0and 50 and the sum of x, y and z is between 2 and 50. The sum of x, yand z can be any number that falls within the range of 2 to 50, e.g., 2,3, 4 . . . 50. This sum can also range from any lower number to anyhigher number within the range of 2 to 50, e.g., 6 to 50, 31 to 50. Thenumbers for x, y, and z are average values and can be partial numbers,e.g., 9.5.

[0061] In another non-limiting embodiment, the naphthopyran isrepresented by graphic formula II wherein:

[0062] (a) R₁₂ is hydrogen;

[0063] (b) R₁₃ is hydrogen or the group, —C(O)J, J being —OR₁₅ or—N(R₁₀)R₁₁, wherein R₁₅ is C₁-C₆ alkyl, phenyl(C₁-C₃)alkyl, or C₁-C₆alkoxy(C₂-C₄)alkyl;

[0064] (c) R₁₄ is hydrogen, C₁-C₆ alkyl, phenyl(C₁-C₃)alkyl, C₁-C₆alkoxy(C₂-C₄)alkyl, C₅-C₇ cycloalkyl, or the group, —C(O)V; wherein V isC₁-C₆ alkyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino; and

[0065] (d) B and B′ are each independently chosen from:

[0066] (i) an unsubstituted, mono-, di-, or tri-substituted phenylgroup;

[0067] (ii) a mono-substituted heteroaromatic group chosen frombenzofuran-2-yl, benzothien-3-yl, dibenzofuranyl, or carbazoyl; each ofsaid phenyl and heteroaromatic substituents in (i) and (ii) beingindependently chosen from —C(O)U, wherein U being C₁-C₆ alkyl, C₁-C₆alkoxy, mono(C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, morpholino, orpiperidino; or amino, mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino,piperidino, morpholino or fluoro;

[0068] (iii) an unsubstituted or mono-substituted phenothiazinyl, saidsubstituents being C₁-C₆ alkyl or C₁-C₆ alkoxy;

[0069] (iv) a monosubstituted phenyl, said phenyl having a substituentlocated at the para position being a linking group, —O—(CH₂)_(r)—,connected to an aryl group which is a member of another photochromicmaterial, and r being chosen from the integer 3 or 6;

[0070] (v) a group represented by one of the following graphic formulae:

[0071]  wherein A being independently chosen in each formula frommethylene or oxygen and D being independently chosen in each formulafrom oxygen or substituted nitrogen, provided that when D is substitutednitrogen, A is methylene; said nitrogen substituents being C₁-C₆ alkyl;each R₂₀ being independently chosen for each occurrence in each formulafrom C₁-C₆ alkyl or C₁-C₆ alkoxy; R₁₈ and R₁₉ each being independentlychosen in each formula from hydrogen or C₁-C₆ alkyl; and q being chosenfrom the integer 0, 1 or 2;

[0072] (vi) C₁-C₆ alkyl, C₃-C₆ cycloalkyl, or C₄-C₁₂ bicycloalkyl;

[0073] (vii) a group represented by the following graphic formula:

[0074]  wherein L being hydrogen and M being an unsubstituted, mono-, ordi-substituted phenyl; each of said group substituents beingindependently chosen from C₁-C₄ alkoxy or fluoro; or

[0075] (viii) B and B′ taken together form fluoren-9-ylidene, mono-, ordi-substituted fluoren-9-ylidene or a saturated C₇-C₁₂ spiro-bicyclichydrocarbon rings; each of said fluoren-9-ylidene substituents beingfluoro.

[0076] In further non-limiting embodiment, the naphthopyran representedby graphic formula II is chosen from:

[0077] (a) 3,3-diphenyl-8-hydroxy-9-carbopropoxy-3H-naphtho[2,1-b]pyran;

[0078] (b)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbopropoxy-3H-naphtho[2,1-b]pyran;

[0079] (c)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;

[0080] (d)3-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;

[0081] (e) 3,3-diphenyl-8-methoxy-9-carbophenoxy-3H-naphtho[2,1-b]pyran;

[0082] (f)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-methoxy-9-carbophenoxy-3H-naphtho[2,1-b]pyran;

[0083] (g)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;

[0084] (h)3-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-8-acetoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;

[0085] (i) 3,3-diphenyl-7-methyl-8-methoxy-3H-naphtho[2,1-b]pyran;

[0086] (j)3-(2-methoxy,4-acryloxyphenyl)-3-(4-methacryloxyphenyl)-8-benzyloxy-9-(carbo-1-indolinyl)-3H-naphtho[2,1-b]pyran;

[0087] (k)3-(2,4,6-trifluorophenyl)-3-(2,4,6-trimethoxy-1-naphthyl)-8-acetyl-9-carboniloyl-3H-naphtho[2,1-b]pyran;

[0088] (l)3-(2-fluorophenyl)-3-(3-methoxy-2-thienyl)-7-h-pentyl-8-benzoyloxy-3H-naphtho[2,1-b]pyran;

[0089] (m)3,3-spiroadamantylene-8-acetoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;

[0090] (n)3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;

[0091] (o)3-(4-methoxyphenyl)-3-(2-phenyl-1-methylvinyl)-8-acetoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;

[0092] (p)3-(4-methoxyphenyl)-3-(9-ethylcarbozol-2-yl)-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;

[0093] (q)3,3-spirofluoren-9-ylidene-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;

[0094] (r)3,3-diphenyl-8-morpholino-9-carbomethoxy-3H-naphtho[2,1-b]pyran; or

[0095] (s) mixtures thereof.

[0096] The materials represented by graphic formula II can be producedby methods known to those skilled in the art, for example, as disclosedin U.S. Pat. Nos. 5,466,398, 5,578,252 and 5,637,262.

[0097] In one non-limiting embodiment, a photochromic material is chosenfrom a naphthopyran represented by the following graphic formula III:

[0098] wherein,

[0099] (a) R₂₁ is the group, —C(O)W or CH₂Q, described hereinbefore in(d) for the material represented by graphic formula I;

[0100] (b) R₂₂ and each R₂₃ are independently chosen for each occurrencefrom hydroxy, NH₂ or N(R)H; wherein R is C₁-C₆ alkyl or aryl and n ischosen from the integers 0, 1, 2, or 3; and

[0101] (c) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0102] In another non-limiting embodiment, the naphthopyran isrepresented by graphic formula III wherein:

[0103] (a) R₂₁ is the group, —C(O)W or CH₂Q, described hereinbefore in(d) for the material represented by graphic formula I;

[0104] (b) R₂₂ and each R₂₃ are independently chosen for each occurrencefrom hydroxy, NH₂ or N(R)H; wherein R is C₁-C₃ alkyl or phenyl and n ischosen from the integers 0, 1 or 2; and

[0105] (c) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0106] In further non-limiting embodiment, the naphthopyran representedby graphic formula III is chosen from:

[0107] (a)2,2-(4-methoxyphenyl)-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;

[0108] (b)2,2-(4-methoxyphenyl)-5-methoxycarbonyl-6-amino-2H-naphtho[1,2-b]pyran;

[0109] (c)2,2-(4-methoxyphenyl)-5-methoxycarbonyl-6-propylamino-2H-naphtho[1,2-b]pyran;

[0110] (d)2-(4-methoxyphenyl)-2-t-butyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;

[0111] (e)2-(4-methoxyphenyl)-2-phenyl-5-methoxycarbonyl-6-amino-2H-naphtho[1,2-b]pyran;

[0112] (f)2,2-(4-methylphenyl)-5-methoxycarbonyl-6-methylamino-2H-naphtho[1,2-b]pyran;

[0113] (g)2,2-diphenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;

[0114] (h)2,2-(4-methoxyphenyl)-5-methoxycarbonyl-6-phenylamino-2H-naphtho[1,2-b]pyran;

[0115] (i)2,2-(4-methoxyphenyl)-5-methoxycarbonyl-6-hydroxy-9-methoxy-2H-naphtho[1,2-b]pyran;

[0116] (j)2,2-diphenyl-5-methoxycarbonyl-6-phenylamino-2H-naphtho[1,2-b]pyran;

[0117] (k)2,2-(3-trifluoromethylphenyl)-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;

[0118] (l)2-(4-methoxyphenyl)-2-(2-methyl,2,3-dihydrobenzofur-5-yl)-5-methoxycarbonyl-6-amino-2H-naphtho[1,2-b]pyran;

[0119] (m)2,2′-spiroadamantylene-5-methoxycarbonyl-6-methoxy-2H-naphtho[1,2-b]pyran;or

[0120] (n) mixtures thereof.

[0121] The materials represented by graphic formula III can be producedby methods known to those skilled in the art, for example, as disclosedin U.S. Pat. Nos. 5,458,814; 5,573,712; 5,650,098; and 5,651,923.

[0122] In one non-limiting embodiment, a photochromic material is chosenfrom a naphthopyran represented by the following graphic formula IV:

[0123] wherein,

[0124] (a) R₅ is the same group described hereinbefore in (d) for thematerial represented by graphic formula I;

[0125] (b) R₂₄ and R₂₅ are each chosen from hydrogen or an amino groupdefined hereinafter, provided that R₂₄ and R₂₅ are not both hydrogen;said amino group being:

[0126] (i) —N(R₁₆)R₁₇, R₁₆ and R₁₇ each being independently chosen fromhydrogen, C₁-C₈ alkyl, aryl, furanyl, benzofuran-2-yl, benzofuran-3-yl,thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl,dibenzothienyl, benzopyridyl, fluorenyl, C₁-C₈ alkylaryl, C₃-C₂₀cycloalkyl, C₄-C₂₀ bicycloalkyl, C₅-C₂₀ tricycloalkyl or C₁-C₂₀alkoxyalkyl and said aryl group being phenyl or naphthyl;

[0127] (ii) a nitrogen containing ring represented by the followinggraphic formula:

[0128] wherein each Y being independently chosen for each occurrencefrom —CH₂—, —CH(R₂₆)—, —C(R₂₆)(R₂₆)—, —CH(aryl)-, —C(aryl)₂— or —C(R₂₆)(aryl)-; X being —Y—, —O—, —S—, —S(O)—, —S(O₂)—, —NH—, —N(R₂₆)— or—N(aryl)-; R₂₆ being C₁-C₆ alkyl; said aryl group being phenyl ornaphthyl, m being chosen from the integer 1, 2 or 3 and p being chosenfrom the integer 0, 1, 2 or 3; provided that when p is 0, X is Y;

[0129] (iii) a group represented by one of the following graphicformulae:

[0130] wherein each R₂₈, R₂₉ and R₃₀ being chosen independently for eachoccurrence in each formula from hydrogen, C₁-C₅ alkyl, phenyl ornaphthyl; or the groups R₂₈ and R₂₉ together form a ring of 5 to 8carbon atoms; R₂₇ being chosen independently for each occurrence fromC₁-C₆ alkyl, C₁-C₆ alkoxy, fluoro or chloro and q being chosen from theinteger 0, 1 or 2;

[0131] (iv) unsubstituted, mono- or di- substituted C₄-C₁₈ spirobicyclicamine; or

[0132] (v) unsubstituted, mono- or di- substituted C₄-C₁₈ spirotricyclicamine; said substituents for (iv) and (v) being independently chosen foreach occurrence from aryl, C₁-C₆ alkyl, C₁-₆ alkoxy orphenyl(C₁-C₆)alkyl; and

[0133] (c) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0134] In another non-limiting embodiment, the naphthopyran isrepresented by graphic formula IV wherein:

[0135] (a) R₅ is chosen from the groups described hereinbefore in (d)for the material represented by graphic formula I;

[0136] (b) R₂₄ and R₂₅ are each chosen from hydrogen or an amino groupdefined hereinafter, provided that R₂₄ and R₂₅ are not both hydrogen;said amino group being:

[0137] (i) —N(R₁₆)R₁₇, R₁₆ and R₁₇ each being independently chosen fromC₁-C₈ alkyl, aryl, or C₃-C₂₀ cycloalkyl; and said aryl group beingphenyl or naphthyl;

[0138] (ii) a nitrogen containing ring represented by the followinggraphic formula:

[0139] wherein each Y being independently chosen for each occurrencefrom —CH₂—, ; X being —Y—, —O—, —S—, or —N(R₂₆)—; R₂₆ being C₁-C₆ alkyl;said aryl group being phenyl or naphthyl, m being chosen from theinteger 1, 2 or 3 and p being chosen from the integer 0, 1, 2 or 3;provided that when p is 0, X is Y; or

[0140] (iii) a group represented by one of the following graphicformulae:

[0141] wherein each R₂₈, R₂₉ and R₃₀ being chosen independently for eachoccurrence in each formula from hydrogen; R₂₇ being chosen independentlyfor each occurrence from C₁-C₆ alkyl, and q being chosen from theinteger 0, 1 or 2; and

[0142] (c) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0143] In a further non-limiting embodiment, the naphthopyranrepresented by graphic formula IV is chosen from:

[0144] (a)2-phenyl-2-(4-morpholinophenyl)-5-carbomethoxy-9-dimethylamino-2H-naphtho[1,2-b]pyran;

[0145] (b)2,2-di(4-methoxyphenyl)-5-methoxymethyl-9-morpholino-2H-naphtho[1,2-b]pyran;

[0146] (c)2-(4-methoxyphenyl)-2-(4-piperidinophenyl)-5-carbomethoxy-9-dimethylamino-2H-naphtho[1,2-b]pyran;or

[0147] (d) mixtures thereof.

[0148] The materials represented by graphic formula IV can be producedby methods known to those skilled in the art, for example, as disclosedin U.S. Pat. Nos. 6,248,264 and 6,348,604.

[0149] In one non-limiting embodiment, a photochromic material is chosenfrom a phenanthropyran represented by one of the following graphicformula VA or VB:

[0150] wherein,

[0151] (a) R₃₁ is the group R₅, described hereinbefore in (d) for thematerial represented by graphic formula I;

[0152] (b) R₃₂ is hydrogen, C₁-C₆ alkyl, C₁-C₆ alkoxy, C₃-C₇ cycloalkyl,pyridyl, phenyl, mono-substituted or di-substituted phenyl, said phenylsubstituents being C₁-C₆ alkyl, C₁-C₆ alkoxy, hydroxy, amino, chloro, orfluoro;

[0153] (c) each R₃₃ is independently chosen for each occurrence fromchloro, fluoro, amino, C₁-C₆ monoalkylamino, —N(R₁₀)R₁₁, as describedhereinbefore in (d) for the material represented by graphic formula I,phenyl, C₁-C₆ alkyl, or —OR₃₄, wherein R₃₄ is hydrogen, C₁-C₆ alkyl,allyl, or acetyl, and q is the integer 0, 1, or 2; and

[0154] (d) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0155] In another non-limiting embodiment, the phenanthropyran isrepresented by graphic formula VA or VB wherein:

[0156] (a) R₃₁ is the group, R₅ described hereinbefore in (d) for thematerial represented by graphic formula I;

[0157] (b) R₃₂ is hydrogen or C₁-C₆ alkyl;

[0158] (c) each R₃₃ is independently chosen for each occurrence from—N(R₁₀)R₁₁, which was described hereinbefore in (d) for the materialrepresented by graphic formula I, C₁-C₆ alkyl, or —OR₃₄, wherein R₃₄ isC₁-C₆ alkyl, and q is the integer 0, 1, or 2; and

[0159] (d) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0160] In a further non-limiting embodiment, the phenanthropyranrepresented by graphic formula VA or VB is chosen from:

[0161] (a)3,3-diphenyl-12-methoxycarbonyl-11-methyl-3H-phenanthro[1,2-b]pyran;

[0162] (b)2,2-diphenyl-5-methoxycarbonyl-6-methyl-2H-phenanthro[4,3-b]pyran;

[0163] (c)2-(4-methoxyphenyl)-2-phenyl-5-methoxycarbonyl-6-methyl-2H-phenanthro[4,3-b]pyran;

[0164] (d)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-6-methoxy-12-methoxycarbonyl-3H-phenanthro[1,2-b]pyran;

[0165] (e)spiro[3H-6-methoxy-12-methoxycarbonylphenanthro[1,2-b]pyran-3-9′-fluorene];

[0166] (f)2,2-di(4-methoxyphenyl)-10-methoxy-5-methoxycarbonyl-6-methyl-2H-phenanthro[4,3-b]pyran;

[0167] (g)3-(2,3-dihydrobenzofur-5-yl)-3-(4-methoxyphenyl)-6-methoxy-12-methoxycarbonyl-11-methyl-3H-phenanthro[1,2-b]pyran;

[0168] (h)3,3-diphenyl-6-methoxy-12-methoxycarbonyl-11-phenyl-3H-phenanthro[1,2-b]pyran;

[0169] (i)3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-6-methoxy-12-methoxycarbonyl-11-phenyl-3H-phenanthro[1,2-b]pyran;

[0170] (j)3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-6-methoxy-12-hydroxymethyl-11-phenyl-3H-phenanthro[1,2-b]pyran;

[0171] (k)2,2-diphenyl-5-N,N-dimethylaminocarbonyl-2H-phenanthro[4,3-b]pyran; or

[0172] (l) mixtures thereof.

[0173] The materials represented by graphic formula V can be produced bymethods known to those skilled in the art, for example, as disclosed inU.S. Pat. No. 5,514,817.

[0174] In one non-limiting embodiment, a photochromic material is chosenfrom a fluoranthenopyran represented by the following graphic formulaVI:

[0175] wherein,

[0176] (a) R₃₅ and R₃₆ are each independently chosen for each occurrencefrom hydroxy, aryl, mono(C₁-C₆)alkoxyaryl, di(C₁-C₆)alkoxyaryl,mono(C₁-C₆)alkylaryl, di(C₁-C₆)alkylaryl, bromoaryl, chloroaryl,fluoroaryl, C₃-C₇ cycloalkylaryl, C₃-C₇ cycloalkyl, C₃-C₇ cycloalkyloxy,C₃-C₇ cycloalkyloxy(C₁-C₆)alkyl, C₃-C₇ cycloalkyloxy(C₁-C₆)alkoxy,aryl(C₁-C₆)alkyl, aryl(C₁-C₆)alkoxy, aryloxy, aryloxy(C₁-C₆)alkyl,aryloxy(C₁-C₆)alkoxy, mono- or di(C₁-C₆)alkylaryl(C₁-C₆)alkyl, mono- ordi(C₁-C₆)alkoxyaryl(C₁-C₆)alkyl, mono- ordi(C₁-C₆)alkylaryl(C₁-C₆)alkoxy, mono- ordi(C₁-C₆)alkoxyaryl(C_(l)-C₆)alkoxy, C₁-C₆ alkyl, C₁-C₆ bromoalkyl,C₁-C₆ chloroalkyl, C₁-C₆ fluoroalkyl, C₁-C₆ alkoxy,mono(C₁-C₆)alkoxy(C₁-C₄)alkyl, acryloxy, methacryloxy, bromo, chloro,fluoro, amino, mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, phenylamino,mono- or di-(C₁-C₆)alkyl substituted phenylamino or mono- ordi-(C₁-C₆)alkoxy substituted phenylamino, and q is the integer 0, 1 or2;

[0177] (b) R₅ is chosen from the group described hereinbefore in (d) forthe material represented by graphic formula I; and

[0178] (c) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0179] In another non-limiting embodiment, the fluoranthenopyran isrepresented by graphic formula VI wherein:

[0180] (a) R₃₅ and R₃₆ are each independently chosen for each occurrencefrom C₁-C₆ alkyl, C₁-C₆ alkoxy, fluoro, amino, mono(C₁-C₆)alkylamino,di(C₁-C₆)alkylamino, phenylamino, mono- or di-(C₁-C₆)alkyl substitutedphenylamino or mono- or di-(C₁-C₆)alkoxy substituted phenylamino, and qis the integer 0, 1 or 2;

[0181] (b) R₅ is chosen from the group described hereinbefore in (d) forthe material represented by graphic formula I; and

[0182] (c) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0183] In a further non-limiting embodiment, the fluoranthenopyranrepresented by graphic formula VI is chosen from:

[0184] (a)5,5-bis(4-methoxyphenyl)-8-ethoxycarbonyl-5H-fluorantheno[3,2-b]pyran;

[0185] (b)5-(4-methoxyphenyl)-5-(4-morpholinophenyl)-8-ethoxycarbonyl-5H-fluorantheno[3,2-b]pyran;

[0186] (c) 5,5-diphenyl-8-ethoxycarbonyl-5H-fluorantheno[3,2-b]pyran;

[0187] (d)5,5-bis(4-methoxyphenyl)-8-methylol-5H-fluorantheno[3,2-b]pyran;

[0188] (e)5,5-bis(4-methoxyphenyl)-2-methoxy-8-methoxycarbonyl-5H-fluorantheno[3,2-b]pyran;or

[0189] (f) mixtures thereof.

[0190] The materials represented by graphic formula VI can be producedby methods known to those skilled in the art, for example, as disclosedin U.S. Pat. No. 5,891,368.

[0191] In one non-limiting embodiment, a photochromic material is chosenfrom a naphthopyran represented by the following graphic formula VII:

[0192] wherein,

[0193] (a) R₃₇ and R₃₈ together form an oxo group or R₃₇ and R₃₈ eachare independently chosen for each occurrence from hydrogen, C₁-C₆ alkyl,C₃-C₇ cycloalkyl, allyl, phenyl, mono- or di-substituted phenyl, benzyl,mono-substituted benzyl, naphthyl, mono- or di-substituted naphthyl,C₄-C₁₂ bicycloalkyl, linear or branched C₃-C₁₂ alkenyl, C₁-C₆ alkoxycarbonyl(C₁-C₆)alkyl, methacryloxy(C₁-C₆)alkyl, acryloxy(C₁-C₆)alkyl,C₁-C₄ acyloxy(C₁-C₆)alkyl, C₁-C₆ alkoxy(C₁-C₆)alkyl or theunsubstituted, mono- or di-substituted heteroaromatic groups pyridyl,furanyl, benzofuran-2-yl, benzyfuran-3-yl, thienyl, benzothien-2-yl,benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazolyl,benzopyridyl and indolyl, each of said phenyl, benzyl, naphthyl andheteroaromatic group substituents being C₁-C₆ alkyl, C₁-C₆ alkoxy,morpholino, di(C₁-C₆)alkylamino, chloro or fluoro;

[0194] (b) R₃₉ is chosen from C₁-C₆ alkyl, C₁-C₆ alkoxy, chloro, fluoro,phenyl, mono- and di-substituted phenyl, benzyl or mono-substitutedbenzyl, C₃-C₇ cycloalkyl, aryloxy, di(C₁-C₆)alkylamino, morpholino,thiomorpholino, piperidino, pyridyl, tetrahydroquinolino, isoquinolino,aziridino, diarylamino, N-(C₁-C₆)alkyl piperizino or N-aryl piperizino,wherein the aryl groups are phenyl or naphthyl, each of said phenyl andbenzyl substituents being C₁-C₆ alkyl, C₁-C₆ alkoxy, fluoro or chloro,and q is the integer 0, 1 or 2;

[0195] (c) I is oxygen or —N(R₄₀)—, wherein R₄₀ is hydrogen C₁-C₆ alkyl,C₃-C₇ cycloalkyl, allyl, vinyl, C₁-C₅ acyl, phenyl, mono- anddi-substituted phenyl, benzyl, mono-substituted benzyl, C₁-C₄alkoxycarbonyl(C₁-C₆)alkyl, methacryloxy(C₁-C₆)alkyl,acryloyloxy(C₁-C₆)alkyl, phenyl(C₁-C₆)alkyl, naphthyl, C₄-C₁₂bicycloalkyl, C₂-C₄ acyloxy or the unsubstituted or substitutedheteroaromatic groups pyridyl, furanyl, benzofuran-2-yl,benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl,dibenzofuranyl, dibenzothienyl, carbazolyl, benzopyridyl or indolyl,each of said phenyl, benzyl and heteroaromatic group substituents beingC₁-C₆ alkyl or C₁-C₆ alkoxy;

[0196] (d) K is oxygen, —N(R₄₀)— or —C(R₄₁)(R₄₂)—, wherein R₄₁ and R₄₂are each hydrogen, C₁-C₆ alkyl or C₃-C₇ cycloalkyl; and

[0197] (e) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0198] In another non-limiting embodiment, the naphthopyran isrepresented by graphic formula VII wherein:

[0199] (a) R₃₇ and R₃₈ together form an oxo group or R₃₇ and R₃₈ eachare independently chosen for each occurrence from hydrogen, C₁-C₆ alkyl,C₃-C₇ cycloalkyl, phenyl or methacryloxy(C₁-C₆)alkyl;

[0200] (b) R₃₉ is chosen from C₁-C₆ alkyl, C₁-C₆ alkoxy, fluoro, ormorpholino, and q is the integer 0, 1 or 2;

[0201] (c) I is oxygen or —N(R₄₀)—, wherein R₄₀ is C₁-C₆ alkyl, C₃-C₇cycloalkyl or phenyl;

[0202] (d) K is oxygen, —N(R₄₀)— or —C(R₄₁)(R₄₂)—, wherein R₄₁ and R₄₂are each hydrogen or C₁-C₆ alkyl; and

[0203] (e) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0204] In a further non-limiting embodiment, the naphthopyranrepresented by graphic formula VII is chosen from:

[0205] a) 7,7-diphenyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran; p0 b)7,7-di(4-methoxyphenyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0206] c)7-(4-methoxyphenyl)-7-phenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0207] d) 7,7-diphenyl-2-ethyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0208] e) 7,7-diphenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0209] f)7,7-diphenyl-2-(2-methylpropyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0210] g) 2,7,7-triphenyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0211] h)7,7-diphenyl-2-(1-phenylethyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0212] i)3-methyl-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;

[0213] j)3-(2-ethoxycarbonylethyl)-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;

[0214] k)3-hexyl-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;

[0215] l)3-(2-methacryloyloxyethyl)-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;

[0216] m)2,2,7,7-tetraphenyl-4-oxo-2,3,4,7-tetrahydro-1H-pyrimidino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0217] n)2,2,7,7-tetraphenyl-4-oxo-2,3,4,7-tetrahydro-1H-[1,3]oxazino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0218] o)7,7-diphenyl-1,2,4,7-tetrahydro-2,2-dimethylpyrano[3′,4′:3,4]naphtho[1,2-b]pyran;

[0219] p)7-phenyl-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0220] q)7-(2-fluorophenyl)-7-(3-methyl-4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0221] r)7-(4-methoxyphenyl)-7-(2,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0222] s)7-(4-morpholino-2-fluorophenyl)-7-(4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0223] t)7-(2-fluoro-4-methoxyphenyl)-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0224] u)7-(4-morpholino-2-fluorophenyl)-7-(3,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;or

[0225] v) mixtures thereof.

[0226] The materials represented by graphic formula VII can be producedby methods known to those skilled in the art, for example, as disclosedin U.S. Pat. No. 6,022,497.

[0227] In one non-limiting embodiment, a photochromic material is chosenfrom a naphthopyran represented by the following graphic formula VIII:

[0228] wherein,

[0229] (a) R₄₃ and R₄₄ together form an oxo group or R₄₃ and R₄₄ areboth hydrogen, C₁-C₆ alkyl, C₃-C₇ cycloalkyl, allyl, phenyl,mono-substituted phenyl, benzyl or mono-substituted benzyl each of saidphenyl and benzyl group substituents being C₁-C₆ alkyl or C₁-C₆ alkoxy;

[0230] (b) R₄₅ is hydrogen, C₁-C₆ alkyl, C₃-C₇ cycloalkyl, or the group,CH(B)B′, wherein B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II;

[0231] (c) R₄₆ is hydrogen, C₁-C₆ alkyl, or C₃-C₇ cycloalkyl;

[0232] (d) each R₄₇ is C₁-C₆ alkyl, C₁-C₆ alkoxy, chloro or fluoro, andq is the integer 0, 1, or 2; and

[0233] (e) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0234] In another non-limiting embodiment, the naphthopyran isrepresented by graphic formula VIII wherein:

[0235] (a) R₄₃ and R₄₄ together form an oxo group or R₄₃ and R₄₄ areboth hydrogen, C₁-C₆ alkyl, C₃-C₇ cycloalkyl or phenyl;

[0236] (b) R₄₅ is hydrogen or C₁-C₆ alkyl;

[0237] (c) R₄₆ is hydrogen or C₁-C₆ alkyl, C₃-C₇ cycloalkyl;

[0238] (d) each R₄₇ is C₁-C₆ alkyl, C₁-C₆ alkoxy or fluoro, and q is theinteger 0, 1 or 2; and

[0239] (e) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0240] In a further non-limiting embodiment, the naphthopyranrepresented by graphic formula VIII is chosen from:

[0241] (a)7,7-diphenyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0242] (b)7,7-di(4-methoxyphenyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0243] (c)7-(4-methoxyphenyl)-7-phenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0244] (d)7,7-diphenyl-2-ethyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0245] (e)7,7-diphenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0246] (f)7,7-diphenyl-2-(2-methylpropyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0247] (g)2,7,7-triphenyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0248] (h)7,7-diphenyl-2-(1-phenylethyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0249] (i)3-methyl-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;

[0250] (j)3-(2-ethoxycarbonylethyl)-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;

[0251] (k)3-hexyl-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;

[0252] (l)3-(2-methacryloyloxyethyl)-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;

[0253] (m)2,2,7,7-tetraphenyl-4-oxo-2,3,4,7-tetrahydro-1H-pyrimidino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0254] (n)2,2,7,7-tetraphenyl-4-oxo-2,3,4,7-tetrahydro-1H-[1,3]oxazino[5′,4′:3,4]naphtho[1,2-b]pyran;

[0255] (o)7,7-diphenyl-1,2,4,7-tetrahydro-2,2-dimethylpyrano[3′,4′:3,4]naphtho[1,2-b]pyran;or

[0256] (p)2-(4-methoxyphenyl)-2-(2,4-dimethoxy-phenyl)-7-diphenylmethyl-10-methyl-5-oxo-2H-5H-pyrano[3′,4′:3,4]naphtho[1,2-b]pyran;or

[0257] (q) mixtures thereof.

[0258] The materials represented by graphic formula VIII can be producedby methods known to those skilled in the art, for example, as disclosedin U.S. Pat. No. 6,106,744.

[0259] In one non-limiting embodiment, a photochromic material is chosenfrom a naphthopyran represented by the following graphic formulae IXA,IXB, IXC, IXD, IXE, IXF, IXG or IXH:

[0260] wherein,

[0261] (a) R₄₃ and R₄₄ are the same groups described hereinbefore in (a)for the represented by graphic formula VIII;

[0262] (b) each R₄₇ and q are the same as described hereinbefore in (d)for the material represented by graphic formula VIII; and

[0263] (c) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0264] In another non-limiting embodiment, the naphthopyran isrepresented by graphic formulae IXA, IXB, IXC, IXD, IXE, IXF, IXG or IXHwherein:

[0265] (a) R₄₃ and R₄₄ are the same groups described hereinbefore in (a)for the material represented by graphic formula VIII;

[0266] (b) each R₄₇ and q are the same as described hereinbefore in (d)for the material represented by graphic formula VIII; and

[0267] (c) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0268] In a further non-limiting embodiment, the naphthopyranrepresented by graphic formula IXA, IXB, IXC or IXD is chosen from:

[0269] a)2,2-bis(4-methoxyphenyl)-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;

[0270] b)6,6-bis(4-methoxyphenyl)-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;

[0271] c)6,6-bis(4-methoxyphenyl)-6,10-dihydro[2]benzopyrano-[3′,4′:3,4]naphtho(1,2-b)pyran;

[0272] d)2-(4-methoxyphenyl)-2-(4-morpholinophenyl)-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,41naphtho(2,1-b)pyran;

[0273] e)6-(4-methoxyphenyl)-6-(4-morpholinophenyl)-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;

[0274] f)10,10-dimethyl-6-(4-methoxyphenyl)-6-(4-morpholinophenyl)-6,10-dihydro[2]benzopyrano[3′,4′:3,4]-naphtho(1,2-b)pyran;

[0275] g)2-(4-morpholinophenyl)-2-phenyl-10-oxo-2,10-dihydro-[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;

[0276] h)6-(4-morpholinophenyl)-6-phenyl-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;

[0277] i)2,2-bis(4-methoxyphenyl)-12,13-dimethoxy-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;

[0278] j)6,6-bis(4-methoxyphenyl)-12,13-dimethoxy-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;

[0279] k)6-(4-methoxyphenyl)-6-phenyl-12,13-dimethoxy-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)-pyran;

[0280] l)2-(4-methoxyphenyl)-2-phenyl-12,13-dimethoxy-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;

[0281] m)6,6-(4-methoxyphenyl)-6-phenyl-12,13-dimethoxy-10,10-dimethyl-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;

[0282] n)2,2-bis(4-methoxphenyl)-12-methoxy-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;

[0283] o)6-bis(4-methoxyphenyl)-12-methoxy-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;

[0284] p)6,6-diphenyl-9-oxo-6,9-dihydro[l]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;

[0285] q)3,3-diphenyl-8-oxo-3,8-dihydro[2]benzopyrano[3′,4′:5,6]naphtho(2,1-b)pyran;or

[0286] r) mixtures thereof.

[0287] The materials represented by graphic formula IXA, IXB, IXC, IXD,IXE, IXF, IXG or IXH can be produced by methods known to those skilledin the art, for example, as disclosed in U.S. Pat. Nos. 6,022,495 and6,149,841.

[0288] In one non-limiting embodiment, a photochromic material is chosenfrom a naphthopyran represented by the following graphic formulae XA orXB:

[0289] wherein,

[0290] (a) A′ is chosen from:

[0291] (i) an unsubstituted, mono-substituted or di-substitutedheterocyclic ring chosen from benzothieno, benzofurano or indolo, the2,3 or 3,2 positions of said heterocyclic ring being fused to the i, jor k side of said naphthopyran represented by graphic formula XA or saidheterocyclic ring is fused to the f side of said naphthopyranrepresented by graphic formula XB; or

[0292] (ii) an unsubstituted, mono-substituted or di-substituted indenogroup fused to the i, j or k side of said naphthopyran represented bygraphic formula XA or to the f side of said naphthopyran represented bygraphic formula XB; each of said heterocyclic ring and indeno groupsubstituents being C₁-C₆ alkyl, C₅-C₇ cycloalkyl, C₁-C₆ alkoxy,—N(R₁₀)R₁₁, which was described hereinbefore in (d) for the materialrepresented by graphic formula I, chloro, fluoro, benzo, mono- ordi-substituted benzo group fused to the benzo portion of thebenzothieno, benzofurano, indeno or indolo moiety, said benzosubstitutent being C₁-C₆ alkyl, C₅-C₇ cycloalkyl, C₁-C₆ alkylmono-substituted (C₅-C₇)cycloalkyl, C₁-C₆ alkoxy, —N(R₁₀)R₁₁, chloro orfluoro;

[0293] (b) R₄₈ is chosen from:

[0294] (i) —C(O)W′, W′ being —OR₉ or —N(R₁₀)R₁₁, which groups weredescribed hereinbefore in (d) for the material represented by graphicformula I; or

[0295] (ii) —C(R₅₁)₂X′, wherein X′ is —CN, chloro, fluoro, hydroxy,benzoyloxy, C₁-C₆ alkoxy, C₂-C₆ acyloxy, amino, C₁-C₆ mono-alkylamino,C₁-C₆ dialkylamino, morpholino, piperidino, 1-indolinyl, pyrrolidyl, ortrimethylsilyloxy, R₅₁ is hydrogen, C₁-C₆ alkyl, phenyl or naphthyl, andeach of said phenyl and heterocyclic ring substituents in this part (b)being C₁-C₆ alkyl or C₁-C₆ alkoxy;

[0296] (c) R₄₉ is hydrogen, C₁-C₆ alkyl, the mono-, di- ortri-substituted aryl groups phenyl or naphthyl, said aryl substituentsbeing C₁-C₆ alkyl, C₁-C₆ alkoxy, chloro or fluoro; or

[0297] (d) each R₅₀ is chloro, fluoro, C₁-C₆ alkyl, C₁-C₆ alkoxy,phenyl, naphthyl, phenoxy, naphthoxy or the group, —N(R₁₀)R₁₁, which wasdescribed hereinbefore in (d) for the material represented by graphicformula I, and q is selected from the integers 0, 1 or 2 in saidnaphthopyran represented by graphic XA, or each R₅₀ is chloro, fluoro,phenoxy, naphthoxy or the group, —N(R₁₀)R₁₁, and p is selected from theintegers 0, 1, 2 or 3 in said naphthopyran represented by graphicformula XB; and

[0298] (e) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0299] In another non-limiting embodiment, the naphthopyran isrepresented by graphic formulae XA or XB wherein:

[0300] (a) A′ is chosen from:

[0301] (i) an unsubstituted, mono- or di-substituted heterocyclic ring;and

[0302] (ii) an unsubstituted or mono-substituted indeno group, each ofsaid heterocyclic ring and indeno group substituents being C₁-C₄ alkyl,C₁-C₃ alkoxy, —N(R₁₀)R₁₁, which was described hereinbefore in (d) forthe material represented by graphic formula I, benzo, mono- ordi-substituted benzo group fused to the indeno moiety, said benzosubstitutents being C₁-C₃ alkyl, C₁-C₃ alkoxy or —N(R₁₀)R₁₁;

[0303] (b) R₄₈ is chosen from:

[0304] (i) —C(O)W′, W′ being —OR₉ or —N(R₁₀)R₁₁, wherein said groupswere described hereinbefore in (d) for the material represented bygraphic formula I; or

[0305] (ii) —C(R₅₁)₂X′, wherein X′ is —CN, halogen, hydroxy, benzoyloxy,C₁-C₄ alkoxy, C₂-C₄ acyloxy, amino, C₁-C₄ mono-alkylamino, C₁-C₄dialkylamino, morpholino, piperidino, 1-indolinyl or pyrrolidyl, and R₅₁is hydrogen, C₁-C₄ alkyl, phenyl or naphthyl;

[0306] (c) R₄₉ is hydrogen, C₁-C₄ alkyl, the mono- or di-substitutedaryl groups phenyl or naphthyl, said aryl substituents being C₁-C₄ alkylor C₁-C₄ alkoxy, chloro or fluoro;

[0307] (d) each R₅₀ is fluoro, C₁-C₄ alkyl, C₁-C₄ alkoxy, phenyl,naphthyl, phenoxy, naphthoxy, or the group, —N(R₁₀)R₁₁, which wasdescribed hereinbefore in (d) for the material represented by graphicformula I, and q is selected from the integers 0, 1 or 2 for thenaphthopyran represented by graphic formula XA or p is selected from theintegers 0, 1, 2 or 3 for the naphthopyran represented by graphicformula XB; and

[0308] (e) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0309] In a further non-limiting embodiment, the naphthopyranrepresented by graphic formula XA or XB is chosen from:

[0310] (a)2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-methyl-2H-benzofuro[2′,3′:7,8]naphtho[12-b]pyran;

[0311] (b)2-(4-methoxyphenyl)-2-(4-propoxyphenyl)-5-methoxycarbonyl-6-methyl-2H-benzofuro[2′,3′:7,8]naphtho[12-b]pyran;

[0312] (c)2,2′-Spiroadamantylene-5-methoxycarbonyl-6-methyl-2H-benzofuro[2′,3′:7,8]naphtho[1,2-b]pyran;

[0313] (d)3,3-Bis(4-methoxyphenyl)-10-methoxy-3H-naphtho[2″,1″:4′,5′]furo[2′,3′:3,4]naphtho[1,2-b]pyran;

[0314] (e)3,3-Bis(4-methoxyphenyl)-3H-naphtho[1″,2″:4′,5′]furo[3′,2′:3,4]naphtho[1,2-b]pyran;

[0315] (f)3,3′-Spiroadamantylene-3H-naphtho[1″,2″:4′,5′]furo[3′,2′:3,4]naphtho[1,2-b]pyran;

[0316] (g)2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-methyl-2H-indeno[3′,2′:7:8]naphtho[1,2-b]pyran;

[0317] (h)3,3-di(4-methoxyphenyl)-6,11-dimethoxy-13-butyl-13-ethoxy-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;

[0318] (i)3,3-di(4-methoxyphenyl)-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;or

[0319] (j) mixtures thereof.

[0320] The materials represented by graphic formula XA or XB can beproduced by methods known to those skilled in the art, for example, asdisclosed in U.S. Pat. No. 5,651,923.

[0321] In one non-limiting embodiment, a photochromic material is chosenfrom a indenonaphthopyran represented by the following graphic formulaeXIA or XIB:

[0322] wherein,

[0323] (a) A″ is an unsubstituted, mono-substituted or di-substitutedheterocyclic ring chosen from furo, thieno, benzothieno, benzofurano andindolo, the 2,3 or 3,2 positions of said heterocyclic ring being fusedto the g, h, i, n, o or p side of said indenonaphthopyran, saidheterocyclic ring substituents being C₁-C₆ alkyl, C₅-C₇ cycloalkyl,C₁-C₆ alkoxy, chloro or fluoro;

[0324] (b) R₅₂ and R₅₃ together form an oxo group, a spiro heterocyclicgroup having 2 oxygen atoms and from 3 to 6 carbon atoms including thespirocarbon atom, or R₅₂ and R₅₃ are each hydrogen, hydroxy, C₁-C₆alkyl, C₃-C₇ cycloalkyl, allyl, phenyl, mono-substituted phenyl, benzyl,mono-substituted benzyl, chloro, fluoro or the group, —C(O)W″, whereineach W″ is hydroxy, C₁-C₆ alkyl, C₁-C₆ alkoxy, phenyl, mono-substitutedphenyl, amino, mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, morpholino,piperidino or pyrrolidyl; or R₅₂ and R₅₃ are each the group, the group,—N(R₁₀)R₁₁, as described hereinbefore in (d) for the materialrepresented by graphic formula I, or —OR₅₄, wherein each R₅₄ is C₁-C₆alkyl, phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkyl substitutedphenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl,C₁-C₆ alkoxy(C₂-C₄)alkyl, C₃-C₇ cycloalkyl, mono(C₁-C₄)alkyl substitutedC₃-C₇ cycloalkyl, C₁-C₆ chloroalkyl, C₁-C₆ fluoroalkyl, allyl, thegroup, —CH(R₅₅)X″, wherein each R₅₅ is hydrogen or C₁-C₃ alkyl, each X″is —CN, —CF₃, or —COOR₅₅, or each R₅₄ is the group, —C(O)Y′, whereineach Y′ is hydrogen, C₁-C₆ alkyl, C₁-C₆ alkoxy, the unsubstituted, mono-or di-substituted aryl groups, phenyl and naphthyl, phenoxy, mono- ordi-(C₁-C₆)alkyl substituted phenoxy, mono- or di-(C₁-C₆)alkoxysubstituted phenoxy, amino, mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino,phenylamino, mono- or di-(C₁-C₆)alkyl substituted phenylamino or mono-or di-(C₁-C₆)alkoxy substituted phenylamino, each of said phenyl, benzyland aryl group substituents being C₁-C₆ alkyl or C₁-C₆ alkoxy;

[0325] (c) each R₄₇ and q are the same as described hereinbefore in (d)for the material represented by graphic formula VIII; and

[0326] (d) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0327] In another non-limiting embodiment, the naphthopyran isrepresented by graphic formulae XIA or XIB wherein:

[0328] (a) A″ is an unsubstituted, mono-substituted or di-substitutedheterocyclic ring chosen from furo, thieno, benzothieno, benzofurano orindolo, the 2,3 or 3,2 positions of said heterocyclic ring being fusedto the p side of said indenonaphthopyran, said heterocyclic ringsubstituents being C₁-C₆ alkyl;

[0329] (b) R₅₂ and R₅₃ together form an oxo group, a spiro heterocyclicgroup having 2 oxygen atoms and from 3 to 6 carbon atoms including thespirocarbon atom, or R₅₂ and R₅₃ are each hydrogen, hydroxy, C₁-C₆alkyl, C₃-C₇ cycloalkyl, phenyl or the group, —C(O)W″, wherein each W″is C₁-C₆ alkoxy, mono(C₁-C₆)alkylamino or di(C₁-C₆)alkylamino, or R₅₂and R₅₃ are each the group, —N(R₁₀)R₁₁, as described hereinbefore in (d)for the material represented by graphic formula I, or —OR₅₄, whereineach R₅₄ is C₁-C₆ alkyl, phenyl(C₁-C₃)alkyl, the group, —CH(R₅₅)X″,wherein each R₅₅ is hydrogen or C₁-C₃ alkyl, each X″ is —COOR₅₅, or eachR₅₄ is the group, —C(O)Y′, wherein each Y′ is C₁-C₆ alkyl;

[0330] (c) each R₄₇ and q are the same as described hereinbefore in (d)for the material represented by graphic formula VIII; and

[0331] (d) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0332] In a further non-limiting embodiment, the naphthopyranrepresented by graphic formula XIA or XIB is chosen from:

[0333] (a)3,3-di(4-methoxyphenyl)-16-hydroxy-16-ethyl-16H-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;

[0334] (b)3,3-di(4-methoxyphenyl)-16-hydroxy-16H-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran;

[0335] (c)3,3-di(4-methoxyphenyl)-16-hydroxy-16-ethyl-16H-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran;or

[0336] (d) mixtures thereof.

[0337] The materials represented by graphic formula XIA or XIB can beproduced by methods known to those skilled in the art, for example, asdisclosed in U.S. Pat. No. 5,698,141.

[0338] In one non-limiting embodiment, a photochromic material is chosenfrom an indenonaphthopyran represented by graphic formulae XITA or XIIBwherein:

[0339] (a) A″ is the same as described hereinbefore in (a) for thematerial represented by graphic formula XIA or XIB;

[0340] (b) R₅₆ is hydrogen, hydroxy, bromo, fluoro or chloro and R₅₇ isthe group, —CH(V′)₂, wherein V′ is —CN or —COOR₅₈, and each R₅₈ ishydrogen, C₁-C₆ alkyl, phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkyl substitutedphenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl orthe unsubstituted, mono- or di-substituted aryl groups phenyl ornaphthyl, or R₅₇ is the group, —CH(R₅₉)Y″, wherein R₅₉ is hydrogen,C₁-C₆ alkyl or the unsubstituted, mono- or di-substituted aryl groupsphenyl or naphthyl, and Y″ is —COOR₅₈, —COR₅₉, or —CH₂OR₆₀, wherein R₅₉is hydrogen, C₁-C₆ alkyl, the unsubstituted, mono- or di-substitutedaryl groups phenyl or naphthyl, amino, mono(C₁-C₆)alkylamino,di(C₁-C₆)alkylamino, phenylamino, mono- or di-(C₁-C₆)alkyl substitutedphenylamino, mono- or di-(C₁-C₆)alkoxy substituted phenylamino,diphenylamino, mono- or di-(C₁-C₆)alkyl substituted diphenylamino, mono-or di-(C₁-C₆)alkoxy substituted diphenylamino, morpholino, orpiperidino; R₆₀ is hydrogen, —COR₅₈, C₁-C₆ alkyl, C₁-C₃alkoxy(C₁-C₆)alkyl, phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkyl substitutedphenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl, orthe unsubstituted, mono- or di-substituted aryl groups phenyl ornaphthyl, each of said aryl group substituents being C₁-C₆ alkyl orC₁-C₆ alkoxy; or

[0341] (c) R₅₆ and R₅₇ together form the group, ═C(V′)₂ or ═C(R₅₉)W′″,wherein W′″ is —COOR₅₈ or —COR₅₉;

[0342] (d) each R₄₇ and q are the same as described hereinbefore in (d)for the material represented by graphic formula VIII; and

[0343] (e) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0344] In another non-limiting embodiment, the naphthopyran isrepresented by graphic formulae XIIA or XIIB wherein:

[0345] (a) A″ is the same as described hereinbefore in (a) for thematerial represented by graphic formula XIA or XIB;

[0346] (b) R₅₆ is hydrogen or hydroxy and R₅₇ is the group, —CH(V′)₂,wherein V′ is —COOR₅₈, and each R₅₈ is C₁-C₆ alkyl orphenyl(C₁-C₃)alkyl; or R₅₇ is the group, —CH(R₅₉)Y″, wherein R₅₉ ishydrogen and Y″ is —COOR₅₈, or —CH₂OR₆₀ wherein R₅₉ is C₁-C₆ alkyl ordi(C₁-C₆)alkylamino; and R₆₀ is C₁-C₆ alkyl; or

[0347] (c) R₅₆ and R₅₇ together form the group, ═C(R₅₉)W′″, wherein W′″is —COOR₅₈;

[0348] (d) each R₄₇ and q are the same as described hereinbefore in (d)for the material represented by graphic formula VIII; and

[0349] (e) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0350] In a further non-limiting embodiment, the naphthopyranrepresented by graphic formula XIIA or XIIB is chosen from:

[0351] (a) 3,3-di(4-methoxyphenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;

[0352] (b)3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;

[0353] (c)3-phenyl-3-(4-methoxyphenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[l,2-b]pyran;

[0354] (d)3-phenyl-3-(4-morpholinophenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran; or

[0355] (e) mixtures thereof.

[0356] The materials represented by graphic formula XIIA or XIIB can beproduced by methods known to those skilled in the art, for example, asdisclosed in U.S. Pat. No. 5,723,072.

[0357] In one non-limiting embodiment, a photochromic material is chosenfrom an indenonaphthopyran represented by the following graphic formulaXIII:

[0358] wherein,

[0359] (a) R₆₁ is represented by:

[0360] (i) —SR₆₇, R₆₇ being chosen from C₁-C₆ alkyl, aryl, mono- ordi-substituted aryl, said aryl group being phenyl or naphthyl and eachof said aryl substituents being chosen independently from C₁-C₆ alkyl,C₁-C₆ alkoxy or halogen;

[0361] (ii) an amino group described hereinbefore in (b) (i), (ii),(iii), (iv) or (v) for the material represented by graphic formula IV;

[0362] (b) R₆₁′ is independently chosen for each occurrence from C₁-C₆alkyl or C₁-C₆ alkoxy and q being chosen from the integer 0, 1 or 2;

[0363] (c) R₆₂ and R₆₃ are each independently chosen from:

[0364] (i) hydrogen, hydroxy, amino, mono- or di-substituted amino,C₁-C₁₂ alkyl, C₃-C₁₂ alkylidene, C₂-C₁₂ alkylidyne, vinyl, C₃-C₇cycloalkyl, C₁-C₆ alkoxyalkyl, allyl, benzyl, mono-substituted benzyl,chloro, fluoro or —C(O)W″, wherein W″ being the same group describedhereinbefore in (b) for the material represented by graphic formula XIAor XIB; said amino substituents in (c) (i) being C₁-C₆ alkyl, phenyl,benzyl or naphthyl; each of said benzyl substituents being C₁-C₆ alkylor C₁-C₆ alkoxy;

[0365] (ii) an unsubstituted, mono- di- or tri-substituted group chosenfrom phenyl, naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl,benzofuranyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl,carbazolyl or indolyl; each of said group substituents in (c) (ii) beingchosen independently for each occurrence from chloro, fluoro, C₁-C₆alkyl or C₁-C₆ alkoxy;

[0366] (iii) a monosubstituted phenyl, said phenyl having a substituentlocated at the para position being as described hereinbefore in (d) (v)for the material represented by graphic formula II;

[0367] (iv) —OR₆₇, R₆₇ being chosen from C₁-C₆ alkyl, C₁-C₆ acyl,phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkyl substituted phenyl(C₁-C₃)alkyl,mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl, C₁-C₆alkoxy(C₂-C₄)alkyl, C₃-C₇ cycloalkyl, mono(C₁-C₄)alkyl substituted C₃-C₇cycloalkyl, C₁-C₆ chloroalkyl, C₁-C₆ fluoroalkyl, allyl,tri(C₁-C₆)alkylsilyl, tri(C₁-C₆)alkoxysilyl, di(C₁-C₆)alkyl(C₁-C₆)alkoxysilyl, di(C₁-C₆)alkoxy(C₁-C₆)alkylsilyl, benzoyl,mono-substituted benzoyl, naphthoyl or mono-substituted naphthoyl; eachof said benzoyl and naphthoyl substituents being independently chosenfrom C₁-C₆ alkyl or C₁-C₆ alkoxy; or R₆₇ being —CH(R₆₈)Q″, wherein R₆₈being chosen from hydrogen or C₁-C₃ alkyl and Q″ being chosen from —CN,—CF₃, or —COOR₆₈; or R₆₇ being —C(O)V″, wherein V″ being chosen fromhydrogen, C₁-C₆ alkoxy, phenoxy, mono- or di-(C₁-C₆)alkyl substitutedphenoxy, mono- or di-(C₁-C₆)alkoxy substituted phenoxy, anunsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl,amino, mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, phenylamino, mono- ordi-(C₁-C₆)alkyl substituted phenylamino, or mono- or di-(C₁-C₆)alkoxysubstituted phenylamino; each of said aryl group substituents beingindependently chosen from C₁-C₆ alkyl or C₁-C₆ alkoxy;

[0368] (v) —CH(Q′″)₂, Q′″ being chosen from —CN or —COOR₆₉ and R₆₉ beingchosen from hydrogen, C₁-C₆ alkyl, phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkylsubstituted phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxy substitutedphenyl(C₁-C₃)alkyl or an unsubstituted, mono- or di-substituted arylgroup, phenyl or naphthyl; each of said aryl group substituents beingindependently chosen from C₁-C₆ alkyl or C₁-C₆ alkoxy;

[0369] (vi) —CH(R₇₀)G″, R₇₀ being chosen from hydrogen, C₁-C₆ alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl, and G″ being chosen from —COOR₆₉, —COR₇₁ or —CH₂OR₇₂, whereinR₇₁ being chosen from hydrogen, C₁-C₆ alkyl, an unsubstituted, mono- ordi-substituted aryl group, phenyl or naphthyl, amino,mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, phenylamino, mono- ordi-(C₁-C₆)alkyl substituted phenylamino, mono- or di-(C₁-C₆)alkoxysubstituted phenylamino, diphenylamino, mono- or di(C₁-C₆)alkylsubstituted diphenylamino, mono- or di(C₁-C₆)alkoxy substituteddiphenylamino, morpholino or piperidino; R₇₂ being chosen from hydrogen,—C(O)R₆₉, C₁-C₆ alkyl, C₁-C₃ alkoxy(C₁-C₆)alkyl, phenyl(C₁-C₃)alkyl,mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl or an unsubstituted,mono- or di-substituted aryl group, phenyl or naphthyl, each of saidaryl group substituents being independently chosen from C₁-C₆ alkyl orC₁-C₆ alkoxy;

[0370] (vii) the group T being the same as described hereinbefore in (d)(i) for the material represented by graphic formula II; or

[0371] (viii) R₆₂ and R₆₃ together form an oxo group or a substituted orunsubstituted spiro-carbocyclic ring containing 3 to 6 carbon atoms or asubstituted or unsubstituted spiro-heterocyclic group containing 1 or 2oxygen atoms and 3 to 6 carbon atoms including the spirocarbon atom,said spiro-carbocyclic ring and spiro-heterocyclic group beingannellated with 0, 1 or 2 benzene rings, said substituents beinghydrogen or C₁-C₆ alkyl;

[0372] (d) R₆₄ is chosen from hydrogen, C₁-C₆ alkyl or the group R_(a)chosen from:

[0373] (i) —OR₇₃, R₇₃ being chosen from phenyl(C₁-C₃)alkyl, C₁-C₆ alkyl,mono(C₁-C₆)alkyl substituted phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxysubstituted phenyl(C₁-C₃)alkyl, C₁-C₆ alkoxy(C₂-C₄)alkyl, C₃-C₇cycloalkyl, mono(C₁-C₄)alkyl substituted C₃-C₇ cycloalkyl, C₁-C₆chloroalkyl, C₁-C₆ fluoroalkyl, allyl or —CH(R₆₈)Q″ described in (c)(i); or

[0374] (ii) an amino group described hereinbefore in (b) (i), (ii),(iii), (iv) or (v) for the material represented by graphic formula IV;

[0375] (e) R₆₅ is chosen from hydrogen, C₁-C₆ alkyl or R_(a), said R_(a)being the same as described hereinbefore in (d);

[0376] (f) R₆₆ is chosen from hydrogen, C₁-C₆ alkyl or R_(a), said R_(a)being the same as described hereinbefore in (d); or

[0377] (g) R₆₅ and R₆₆ together form one of the following graphicformulae:

[0378] wherein J′ and K′ being independently chosen for each occurrencein each formula from oxygen or —N(R₁₅)—, said groups R₁₅, R₁₈ and R₁₉each being the same as described hereinbefore in (b) and (d) (vi) forthe material represented by graphic formula II;

[0379] (h) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0380] In another non-limiting embodiment, the indenonaphthopyran isrepresented by graphic formula XIII wherein:

[0381] (a) R₆₁ is represented by:

[0382] (i) —SR₆₇, R₆₇ being C₁-C₆ alkyl or aryl;

[0383] (ii) an amino group described hereinbefore in (b) (i), (ii) or(iii) for the material represented by graphic formula IV;

[0384] (b) R₆₁′ is independently chosen for each occurrence from C₁-C₆alkyl or C₁-C₆ alkoxy and q being the integer 1;

[0385] (c) R₆₂ and R₆₃ are each independently chosen from:

[0386] (i) hydrogen, hydroxy, C₁-C₁₂ alkyl, C₃-C₁₂ alkylidene, C₃-C₇cycloalkyl, or —C(O)W″, wherein W″ being the same group describedhereinbefore in (b) for the material represented by graphic formula XIAor XIB;

[0387] (ii) an unsubstituted, mono- di- or tri-substituted group chosenfrom phenyl; each of said phenyl substituents in (c) (ii) being chosenindependently for each occurrence from chloro, fluoro, C₁-C₆ alkyl orC₁-C₆ alkoxy;

[0388] (iii) a monosubstituted phenyl, said phenyl having a substituentlocated at the para position being as described hereinbefore in (d) forthe material represented by graphic formula II;

[0389] (iv) —OR₆₇, R₆₇ being chosen from C₁-C₆ alkyl,phenyl(C₁-C₃)alkyl, C₁-C₆ alkoxy(C₂-C₄)alkyl or tri(C₁-C₆)alkylsilyl;

[0390] (v) —CH(Q′″)₂, Q′″ being chosen from —COOR₆₉ and R₆₉ being C₁-C₆alkyl;

[0391] (vi) —CH(R₇₀)G″, R₇₀ being chosen from hydrogen, C₁-C₆ alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl, and G″ being chosen from —COOR₆₉, —COR₇₁ or —CH₂OR₇₂, whereinR₇₁ being chosen from hydrogen, C₁-C₆ alkyl, an unsubstituted, mono- ordi-substituted aryl group, phenyl or naphthyl, amino,mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, phenylamino, mono- ordi-(C₁-C₆)alkyl substituted phenylamino, mono- or di-(C₁-C₆)alkoxysubstituted phenylamino, diphenylamino, mono- or di(C₁-C₆)alkylsubstituted diphenylamino, mono- or di(C₁-C₆)alkoxy substituteddiphenylamino, morpholino or piperidino; R₇₂ being chosen from hydrogen,—C(O)R₆₉, C₁-C₆ alkyl, C₁-C₃ alkoxy(C₁-C₆)alkyl, phenyl(C₁-C₃)alkyl,mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl or an unsubstituted,mono- or di-substituted aryl group, phenyl or naphthyl, each of saidaryl group substituents being independently chosen from C₁-C₆ alkyl orC₁-C₆ alkoxy;

[0392] (vii) the group T described hereinbefore in (d) (i) for thematerial represented by graphic formula II; or

[0393] (viii) R₆₂ and R₆₃ together form an oxo group or a substituted orunsubstituted spiro-carbocyclic ring containing 3 to 6 carbon atoms or asubstituted or unsubstituted spiro-heterocyclic group containing 1 or 2oxygen atoms and 3 to 6 carbon atoms including the spirocarbon atom,said spiro-carbocyclic ring and spiro-heterocyclic group beingannellated with 0, 1 or 2 benzene rings, said substituents beinghydrogen or C₁-C₆ alkyl;

[0394] (d) R₆₄ is chosen from hydrogen, C₁-C₆ alkyl or the group R_(a)chosen from:

[0395] (i) —OR₇₃, R₇₃ being chosen from phenyl(C₁-C₃)alkyl, C₁-C₆ alkyl,mono(C₁-C₆)alkyl substituted phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxysubstituted phenyl(C₁-C₃)alkyl, C₁-C₆ alkoxy(C₂-C₄)alkyl, C₃-C₇cycloalkyl, mono(C₁-C₄)alkyl substituted C₃-C₇ cycloalkyl, C₁-C₆chloroalkyl, C₁-C₆ fluoroalkyl, allyl or —CH(R₆₈)Q″; or

[0396] (ii) an amino group described hereinbefore in (b) (i), (ii) or(iii) for the material represented by graphic formula IV;

[0397] (e) R₆₅ is chosen from hydrogen, C₁-C₆ alkyl or R_(a), said R_(a)being the same as described hereinbefore in (d);

[0398] (f) R₆₆ is chosen from hydrogen, C₁-C₆ alkyl or R_(a), said R_(a)being the same as described hereinbefore in (d); or

[0399] (g) R₆₅ and R₆₆ together form one of the following graphicformulae:

[0400]  wherein J′ and K′ being independently chosen for each occurrencein each formula from oxygen or —N(R₁₅)—, said groups R₁₅, R₁₉ and R₂₀each being the same as described hereinbefore in (b) and (d) (vi) forthe material represented by graphic formula II;

[0401] (h) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II

[0402] In a further non-limiting embodiment, the indenonaphthopyranrepresented by graphic formula XIII is chosen from:

[0403] (a)3,3-di(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;

[0404] (b)3-phenyl-3-(4-morpholino-phenyl)-11-morpholino-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho-[1,2-b]pyran;

[0405] (c)3,3-di(4-(2-methoxyethoxyphenyl))-11-morpholino-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;

[0406] (d)3,3-di(4-methoxyphenyl)-11-morpholino-13-hydroxy-13-ethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;

[0407] (e)3,3-di(4-methoxyphenyl)-10-methoxy-11-morpholino-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;

[0408] (f)3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-10-methoxy-11-morpholino-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;

[0409] (g) 3-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)- 11-morpholino-13,13- dimethyl-3H,13H-indeno [2′,3′:3,4]naphtho[1,2-b]pyran;

[0410] (h)3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-11-morpholino-13,13-dimethyl-3H,13H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;

[0411] (i)3-(4-methoxyphenyl)-3-phenyl-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;

[0412] (j)3,3-di(2-methoxyethoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;or

[0413] (k) mixtures thereof.

[0414] The materials represented by graphic formula XIII can be producedby the methods disclosed in U.S. patent application Ser. No. ______filed even herewith on Mar. 20, 2003, which disclosure is incorporatedherein by reference.

[0415] In one non-limiting embodiment, a photochromic material is chosenfrom a indenonaphthopyran represented by the following graphic formulaXIV:

[0416] wherein,

[0417] (a) R₇₄ and R₇₅ are each the same as R₆₂ and R₆₃ groups describedhereinbefore in (c) for the material represented by graphic formulaXIII;

[0418] (b) each R₇₆ is independently chosen for each occurrence fromdi(C₁-C₆)alkylamino, dicyclohexylamino, diphenylamino, piperidyl,morpholinyl, pyridyl, a group T, described hereinbefore in (d) (i) forthe material represented by graphic formula II, and group —C(O)W″described hereinbefore in (b) for the material represented by graphicformula XIII, and q is the integer 0, 1, or 2; or when q is 2, and theR₇₆ substituents are adjacent, each pair of substituents independentlyforms a substituted or unsubstituted fused carbocyclic or heterocyclicring chosen from benzo, pyridino, pyrazino, pyrimidino, furano,dihydrofurano, 1,3-dioxolo, 1,4-dioxolo, 1,3-dioxino, 1,4-dioxino,thiopheno, benzofuro, benzothieno, indolo, or indeno, the substituentsof said fused carbocyclic or heterocyclic ring being chosen fromhalogen, C₁-C₆ alkyl, C₁-C₆ alkoxy, amino, mono- or di-substitutedamino, said amino substituents being chosen from C₁-C₆ alkyl, phenyl,benzyl or naphthyl; said first R₇₆ ring being fused to the o, p or qside and said second R₇₆ ring being fused to the g, h, or i side of theindenonaphthopyran;

[0419] (c) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0420] In another non-limiting embodiment, the indenonaphthopyran isrepresented by graphic formula XIV wherein:

[0421] (a) R₇₄ and R₇₅ are each the same as R₆₂ and R₆₃ groups describedhereinbefore in (c) for the material represented by graphic formulaXIII;

[0422] (b) each R₇₆ is independently chosen from di(C₁-C₆)alkylamino,dicyclohexylamino, diphenylamino, piperidyl, morpholinyl, pyridyl,halogen, or group —C(O)W″ described hereinbefore in (d) for the materialrepresented by graphic formula XIII, and q is the integer 0, 1, or 2; orwhen q is 2, and the R₇₆ substituents are adjacent, each pair ofsubstituents independently forms a substituted or unsubstituted fusedcarbocyclic or heterocyclic ring chosen from benzo, dihydrofurano,1,4-dioxolo, 1,3-dioxino, or benzofuro, the substituents of said fusedcarbocyclic or heterocyclic ring being chosen from the group consistingof C₁-C₆ alkyl or C₁-C₆ alkoxy;

[0423] (c) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (d) for the material represented by graphicformula II.

[0424] In a further non-limiting embodiment, the indenonaphthopyranrepresented by graphic formula XIV is chosen from:

[0425] (a)3,3,9-triphenyl-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0426] (b)3,3-di(4-methoxyphenyl)-9-phenyl-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0427] (c)3-(4-methoxyphenyl)-3,9-diphenyl-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0428] (d)3-(4-morpholinophenyl)-3,9-diphenyl-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0429] (e)3-(4-methoxyphenyl)-3-phenyl-9-methyl-13-methoxy-9-(3-methoxyphenyl)-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0430] (f)3,3-di(4-methoxyphenyl)-9-methyl-13-methoxy-9-(3-methoxyphenyl)-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0431] (g)3,3-di(4-methoxyphenyl)-9-methyl-11-methoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0432] (h)3,3-di(4-methoxyphenyl)-9,9-dimethyl-11-methoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0433] (i)3-(4-methoxyphenyl)-3-phenyl-9,9-dimethyl-11-methoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0434] (j)3,3-di(4-methoxyphenyl)-9,9-dimethyl-7,11-dimethoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0435] (k)3-(4-methoxyphenyl)-3-phenyl-9,9-dimethyl-7,11-dimethoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0436] (l)3-(4-morpholinophenyl)-3-phenyl-9,9-dimethyl-7,11-dimethoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0437] (m)3,3-di(4-methoxyphenyl)-9-methyl-11,13-dimethoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0438] (n)3-(4-methoxyphenyl)-3-phenyl-9-methyl-11,13-dimethoxy-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0439] (o)3-(4-methoxyphenyl)-3-phenyl-9,9-dimethyl-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;

[0440] (p)3,3-di(4-methoxyphenyl-9,9-dimethyl-11-fluoro-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;or

[0441] (q) mixtures thereof.

[0442] The materials represented by graphic formula XIV can be producedby the methods disclosed in U.S. patent application Ser. No. 10/039984filed on Oct. 29, 2001, which disclosure is incorporated herein byreference.

[0443] BWS photochromic materials, including those represented bygraphic formulae I-IVX or a mixture thereof can be used in variousnon-limiting applications in which photochromic materials can beemployed, such as optical lenses, e.g., vision correcting ophthalmiclenses and plane lenses, face shields, goggles, visors, camera lenses,windows, automotive windshields, aircraft and automotive transparencies,e.g., T-roofs, sidelights and backlights, polymeric coatings, plasticfilms and sheets, textiles and pigmented liquids or pastes, e.g., paintsand inks used as verification marks on security documents, e.g.,documents such as banknotes, passports and drivers' licenses for whichauthentication or verification of authenticity may be desired.

[0444] In one non-limiting embodiment, it is contemplated that the BWSphotochromic materials of the present invention can each be used aloneor in combination with other BWS photochromic materials of the presentinvention, or in combination with one or more other photochromicmaterials, e.g., photochromic materials having at least one activatedabsorption maxima within the range of between about 400 and 700nanometers, and can be incorporated, e.g., dissolved or dispersed, in apolymeric organic host material used to prepare photochromic articles,which become colored when activated to an appropriate hue.

[0445] In one non-limiting embodiment, the other photochromic materialscan include the following classes of materials: chromenes, e.g.,naphthopyrans, benzopyrans, indenonaphthopyrans and phenanthropyrans;spiropyrans, e.g., spiro(benzindoline)naphthopyrans,spiro(indoline)benzopyrans, spiro(indoline)naphthopyrans,spiro(indoline)quinopyrans and spiro(indoline)pyrans; oxazines, e.g.,spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines,spiro(benzindoline)pyridobenzoxazines, spiro(benzindoline)naphthoxazinesand spiro(indoline)benzoxazines; mercury dithizonates, fulgides,fulgimides and mixtures of such photochromic materials.

[0446] Such photochromic materials and complementary photochromicmaterials are described in U.S. Pat. No. 4,931,220 at column 8, line 52to column 22, line 40; U.S. Pat. No. 5,645,767 at column 1, line 10 tocolumn 12, line 57; U.S. Pat. No. 5,658,501 at column 1, line 64 tocolumn 13, line 17; U.S. Pat. No. 6,153,126 at column 2, line 18 tocolumn 8, line 60; U.S. Pat. No. 6,296,785 at column 2, line 47 tocolumn 31, line 5; U.S. Pat. No. 6,348,604 at column 3, line 26 tocolumn 17, line 15; and U.S. Pat. No. 6,353,102 at column 1, line 62 tocolumn 11, line 64, the disclosures of the aforementioned patents areincorporated herein by reference. Spiro(indoline)pyrans are alsodescribed in the text, Techniques in Chemistry, Volume III,“Photochromism”, Chapter 3, Glenn H. Brown, Editor, John Wiley and Sons,Inc., New York, 1971.

[0447] In another non-limiting embodiment, polymerizable photochromicmaterials, such as polymerizable naphthoxazines disclosed in U.S. Pat.No. 5,166,345 at column 3, line 36 to column 14, line 3; polymerizablespirobenzopyrans disclosed in U.S. Pat. No. 5,236,958 at column 1, line45 to column 6, line 65; polymerizable spirobenzopyrans andspirobenzothiopyrans disclosed in U.S. Pat. No. 5,252,742 at column 1,line 45 to column 6, line 65; polymerizable fulgides disclosed in U.S.Pat. No. 5,359,085 at column 5, line 25 to column 19, line 55;polymerizable naphthacenediones disclosed in U.S. Pat. No. 5,488,119 atcolumn 1, line 29 to column 7, line 65; polymerizable spirooxazinesdisclosed in U.S. Pat. No. 5,821,287 at column 3, line 5 to column 11,line 39; polymerizable polyalkoxylated naphthopyrans disclosed in U.S.Pat. No. 6,113,814 at column 2, line 23 to column 23, line 29; and thepolymerizable photochromic compounds disclosed in WO97/05213 andapplication Ser. No. 09/828,260 filed Apr. 6, 2001 can be used. Thedisclosures of the aforementioned patents on polymerizable photochromicmaterials are incorporated herein by reference.

[0448] Other non-limiting embodiments of photochromic materials that canbe used include organo-metal dithiozonates, e.g., (arylazo)-thioformicarylhydrazidates, e.g., mercury dithizonates which are described in, forexample, U.S. Pat. No. 3,361,706 at column 2, line 27 to column 8, line43; and fulgides and fulgimides, e.g., the 3-furyl and 3-thienylfulgides and fulgimides, which are described in U.S. Pat. No. 4,931,220at column 1, line 39 through column 22, line 41, the disclosures ofwhich are incorporated herein by reference.

[0449] An additional non-limiting embodiment is a form of organicphotochromic material resistant to the effects of a polymerizationinitiator that can also be used in the photochromic articles of thepresent invention. Such organic photochromic materials includephotochromic compounds encapsulated in metal oxides, the latter of whichare described in U.S. Pat. Nos. 4,166,043 and 4,367,170 at column 1 line36 to column 7, line 12, which disclosure is incorporated herein byreference.

[0450] In another non-limiting embodiment, inorganic photochromicsystems contemplated for use with the BWS materials of the presentinvention typically contain crystallites of silver halide, cadmiumhalide and/or copper halide. Other non-limiting inorganic photochromicglass systems can be prepared by the addition of europium (II) and/orcerium (III) to a soda-silica glass. Such inorganic photochromic glasssystems are described in Kirk Othmer Encyclopedia of ChemicalTechnology, 4th Edition, Volume 6, pages 322-325, which disclosure isincorporated herein by reference.

[0451] The photochromic materials described herein, e.g., the BWSmaterials of the present invention and other photochromic materials, canbe chosen from a variety of materials. Non-limiting examples include: ofcourse, a single photochromic compound; a mixture of photochromiccompounds; a material comprising at least one photochromic compound,such as a plastic polymeric resin or an organic monomeric or oligomericsolution; a material such as a monomer or polymer to which at least onephotochromic compound is chemically bonded; a material comprising and/orhaving chemically bonded to it at least one photochromic compound, theouter surface of the material being encapsulated (encapsulation is aform of coating), for example with a polymeric resin or a protectivecoating such as a metal oxide that prevents contact of the photochromicmaterial with external materials such as oxygen, moisture and/orchemicals that have a negative effect on the photochromic material, suchmaterials can be formed into a particulate prior to applying theprotective coating as described in U.S. Pat. Nos. 4,166,043 and4,367,170; a photochromic polymer, e.g., a photochromic polymercomprising photochromic compounds bonded together; or mixtures thereof.

[0452] The organic photochromic materials and BWS materials of thepresent invention to be used in a photochromic article can be associatedwith a polymeric organic host material or other substrate by variousmeans. In a series of non-limiting embodiments, they can beincorporated, e.g., dissolved and/or dispersed, into the host material,polymerized with other components of the host material, e.g., in areaction injection molding, and/or incorporated into an at least partialcoating or film applied to a substrate, e.g., an at least partiallycured polymeric coating or a film applied to one surface of thesubstrate.

[0453] In one non-limiting embodiment, a photochromic article adapted toretain at least 12 percent of the delta OD measured in the Outdoor Testwhen tested in the Behind the Windshield Test can be prepared by amethod comprising:

[0454] a) obtaining a substrate;

[0455] b) obtaining a photochromic material adapted to change from anunactivated form to an activated form by exposure to radiationsubstantially in the wavelength range from 380 to 410 nanometers whenmeasured over a range of from 380 to 700 nanometers;

[0456] c) introducing the photochromic material together with saidsubstrate by a method chosen from:

[0457] i) introducing photochromic material (b) with the startingmaterials used to form said substrate;

[0458] ii) at least partially imbibing photochromic material (b) into atleast one surface of said substrate;

[0459] iii) applying at least a partial coating of a polymeric coatingcomposition comprising photochromic material (b) to at least one surfaceof said substrate;

[0460] iv) at least partially connecting a superstrate comprisingphotochromic material (b) to at least one surface of said substrate; or

[0461] v) combinations of i), ii), ii) or iv).

[0462] In another non-limiting embodiment, the aforementioned methodfurther comprises adding a photochromic material (c) that is differentfrom photochromic material (b), in (c) (i), (ii), (iii), (iv) or (v). Ina further non-limiting embodiment, the aforementioned method furthercomprises adding a fixed tint dye in (c) (i), (ii), (iii), (iv) or (v).

[0463] An alternate non-limiting embodiment for producing a photochromicarticle adapted to exhibit an unactivated state luminous transmittanceof greater than 70 percent at 23° C., an activated state luminoustransmittance at saturation less than 30 percent when activated at 23°C. by simulated sunlight from a xenon arc lamp set at 6.7 Watts/meter²UVA and 50,000 lumens/meter², and an activated state luminoustransmittance at saturation less than 60 percent when activated at 28°C. by simulated sunlight from a xenon arc lamp through an UV blockingtransparency rendering an irradiance integrated between 380 and 420nanometers of 0.75 Watts/meter² and 1,700 lumens/meter²; said methodcomprising:

[0464] a) obtaining a substrate;

[0465] b) obtaining a photochromic material adapted to change from anunactivated form to an activated form by exposure to radiationsubstantially in the wavelength range from 380 to 410 nanometers whenmeasured over a range of from 380 to 700 nanometers;

[0466] c) introducing the photochromic material with said substrate by amethod chosen from:

[0467] i) introducing photochromic material (b) with the startingmaterials used to form the substrate;

[0468] ii) at least partially imbibing photochromic material (b) into atleast one surface of the substrate;

[0469] iii) applying at least a partial coating of a polymeric coatingcomposition comprising photochromic material (b) to at least one surfaceof the substrate;

[0470] iv) at least partially connecting a superstrate comprisingphotochromic material (b) to at least one surface of the substrate; or

[0471] v) a combination of i), ii), ii) or iv).

[0472] In another non-limiting embodiment, the aforementioned methodfurther comprises adding a photochromic material (c) that is differentfrom photochromic material (b), in (c) (i), (ii), (iii), (iv) or (v). Ina further non-limiting embodiment, the aforementioned method furthercomprises adding a fixed tint dye in (c) (i), (ii), (iii), (iv) or (v).

[0473] The photochromic articles prepared by the aforementioned methodscan be substantially free of ultraviolet radiation absorbing materialsadapted to substantially inhibit the activation of the photochromicmaterial by radiation below 380 nm.

[0474] Potential substrates for the application of coatings containingBWS photochromic materials or a mixture of BWS photochromic materialsand other photochromic include any type of material. Non-limitingexamples include, paper, glass, ceramics, wood, masonry, textiles,metals and polymeric organic host materials.

[0475] Each of the BWS photochromic materials with or without the otherphotochromic materials described herein can be used in amounts (or in aratio) such that a host material or substrate to which the BWSphotochromic materials or mixture of BWS photochromic materials andother photochromics is associated, exhibits a desired resultant color,e.g., a substantially neutral color when activated with unfilteredsunlight, e.g., as near a neutral color as possible given the colors ofthe activated photochromic materials, and a retained coloration,measured as delta OD or ΔOD, of at least 12 percent of that demonstratedunder conditions of outdoor exposure when tested in the Behind theWindshield Test described herein in Example 13. In an alternatenon-limiting embodiment, the photochromic articles of the presentinvention demonstrate an activated state luminous transmittance atsaturation less than 60 percent when activated under the conditions inthe Behind the Windshield Test. In one non-limiting embodiment, the BWSphotochromic materials could be used to produce articles having a widerange of colors, e.g., pink. Further discussion of neutral colors andways to describe colors can be found in U.S. Pat. No. 5,645,767 column12, line 66 to column 13, line 19.

[0476] In one non-limiting embodiment, the amount of the BWSphotochromic materials to be applied to or incorporated into a polymericcoating composition and/or polymeric host material of the photochromicarticle of the present invention can vary widely. Typically, asufficient amount is used to produce the desired retained colorationbehind an UV blocking transparency such as a vehicular windshield.Generally such an amount can be described as a behind the UV blockingtransparency activating amount or behind the windshield activatingamount. The particular amount used depends often upon the retainedcoloration desired upon irradiation thereof and upon the method used toincorporate or apply the BWS photochromic materials. Typically, in onenon-limiting embodiment, the more BWS photochromic material applied orincorporated, the greater is the coloration retained behind thewindshield up to a certain limit. There is a point after which theaddition of any more material will not have a noticeable effect,although more material can be added, if desired

[0477] In one non-limiting embodiment, the amount of the otherphotochromic materials to be incorporated into a polymeric coatingcomposition and/or polymeric host material can vary widely. Typically, asufficient amount is used to produce a photochromic effect discernibleto the naked eye upon activation. Generally such amount can be describedas a photochromic amount. The particular amount used depends often uponthe intensity of color desired upon irradiation thereof and upon themethod used to incorporate the photochromic materials. Typically, in onenon-limiting embodiment, the more photochromic incorporated, the greateris the color intensity up to a certain limit. There is a point afterwhich the addition of any more material will not have a noticeableeffect, although more material can be added, if desired.

[0478] The relative amounts of the aforesaid BWS photochromic materialsor combinations of BWS photochromic materials and other photochromicmaterials used will vary and depend in part upon the relativeintensities of the color of the activated species of such materials, theultimate color desired, the retained coloration desired and the methodof application to the host material and/or substrate. In onenon-limiting embodiment, the amount of total photochromic material whichincludes BWS photochromic materials, other photochromic materials orboth, incorporated by imbibition into a photochromic optical hostmaterial can vary widely. In alternate non-limiting embodiments, it canrange from about 0.01 to about 2.0, or from 0.05 to about 1.0,milligrams per square centimeter of surface to which the photochromicmaterial is incorporated or applied. The amount of total photochromicmaterial incorporated or applied to the host material can range betweenany combination of these values, inclusive of the recited range, e.g.,0.015 to 1.999 milligrams per square centimeter.

[0479] In another non-limiting embodiment, the total amount ofphotochromic material incorporated into a polymerizable composition forforming a coating, film or polymerizate can vary widely, e.g., it canrange from 0.01 to 40 weight percent based on the weight of the solidsin the polymerizable composition. In alternate non-limiting embodiments,the concentration of photochromic materials ranges from 0.1 to 30 weightpercent, from 1 to 20 weight percent, from 5 to 15 weight percent, orfrom 7 to 14 weight percent. The amount of photochromic material in thecoating can range between any combination of these values, inclusive ofthe recited range, e.g., 0.011 to 39.99 weight percent.

[0480] In one non-limiting embodiment, compatible (chemically andcolor-wise) tints, e.g., dyes, can be added or applied to the hostmaterial used to produce the photochromic article to achieve a moreaesthetic result, for medical reasons, or for reasons of fashion. Theparticular dye selected will vary and depend on the aforesaid need andresult to be achieved. In one non-limiting embodiment, the dye can beselected to complement the color resulting from the activatedphotochromic materials, e.g., to achieve a more neutral color or absorba particular wavelength of incident light. In another non-limitingembodiment, the dye can be selected to provide a desired hue to the hostmaterial when the photochromic materials are in an unactivated state.

[0481] In various non-limiting embodiments, adjuvant materials can alsobe incorporated into host material used to produce the photochromicarticle. Such adjuvants can be used, prior to, simultaneously with orsubsequent to application or incorporation of the photochromic material.For example, ultraviolet light absorbers can be admixed withphotochromic materials before their addition to the composition or suchabsorbers can be superposed, e.g., superimposed, as a coating betweenthe photochromic article and the incident light.

[0482] Further, stabilizers can be admixed with the photochromicmaterials prior to their addition to the composition to improve thelight fatigue resistance of the photochromic materials provided thatsuch stabilizers do not prevent the photochromic materials fromactivating. Non-limiting examples of stabilizers include hindered aminelight stabilizers (HALS), asymmetric diaryloxalamide (oxanilide)compounds and singlet oxygen quenchers, e.g., a nickel ion complex withan organic ligand, polyphenolic antioxidants or mixtures of suchstabilizers are contemplated. In one non-limiting embodiment, they canbe used alone or in combination. Such stabilizers are described in U.S.Pat. Nos. 4,720,356, 5,391,327 and 5,770,115.

[0483] The BWS photochromic materials, other photochromic materials orcombinations thereof can be associated with the host material by variousmethods described in the art. In various non-limiting embodiments, thetotal amount of photochromic material can be incorporated into the hostmaterial used to form the photochromic article by various methods suchas by adding the photochromic materials to one or more of the materialsused to form the host material. In one non-limiting embodiment when thehost material is a polymeric coating or film, the photochromic materialscan be dissolved and/or dispersed in an aqueous or organic solvent priorto being incorporated into one or more of the components of the coatingor film composition used to form the coating Alternatively, thephotochromic materials can be incorporated into the at least partiallycured coating or film by imbibition, permeation or other transfermethods as known by those skilled in the art.

[0484] When at least partially cured polymers or polymerizates are usedas the host material for the photochromic materials, variousnon-limiting embodiments include preparation of a photochromic articleby injecting a polymerizable composition with photochromic materialsinto a mold and polymerizing it by what, for example, is commonlyreferred to in the art as a cast-in-place process. Polymerizates, e.g.,lenses, prepared by cast polymerization in the absence of a photochromicamount of a photochromic material can be used to prepare photochromicarticles by applying or incorporating photochromic materials into thepolymerizate by art-recognized methods.

[0485] Such non-limiting art-recognized methods include: (a) dissolvingor dispersing the photochromic materials within the polymerizate, e.g.,imbibition of the photochromic materials into the polymerizate byimmersion of the polymerizate in a hot solution of the photochromicmaterials or by thermal transfer; (b) providing the photochromicmaterial as a separate layer between adjacent layers of thepolymerizate, e.g., as a part of a polymer film; and (c) applying thephotochromic material as part of a coating or film placed or laminatedon the surface of the polymerizate. The term “imbibition” or “imbibe” isintended to mean and include permeation of the photochromic materialsindividually or with other non-photochromic materials into thepolymerizate, solvent assisted transfer absorption of the photochromicmaterials into a polymerizate, vapor phase transfer, and other suchtransfer mechanisms.

[0486] In the context of the present invention, the nature of thepolymeric substrate, polymeric film or polymeric coating, collectivelyreferred to as the polymeric host, can vary widely. Generally thepolymeric host is such that it allows the BWS materials of the presentinvention and other photochromic materials to reversibly transformbetween their “open” and “closed” forms. In one non-limiting embodiment,the polymer and/or polymeric coating composition used to produce thephotochromic articles of the present invention comprises compositionsadapted to provide thermoplastic or thermosetting organic polymericmaterials that are described in the Kirk-Othmer Encyclopedia of ChemicalTechnology, Fourth Edition, Volume 6, pages 669 to 760, which disclosureis incorporated herein by reference. Such polymeric host materials canbe transparent, translucent or opaque; but desirably are transparent. Inanother non-limiting contemplated embodiment is a polymeric materialthat upon curing forms an at least partially cured polymeric coatingchosen from polyurethanes, aminoplast resins, poly(meth)acrylates, e.g.,polyacrylates and polymethacrylates, polyanhydrides, polyacrylamides,epoxy resins and polysilanes.

[0487] The various coating compositions described below are well knownand are made with components and according to methods well understoodand appreciated to those skilled in the art. Suitable substrates for theapplication of coatings containing the BWS materials or a mixture of theBWS materials and other photochromic materials include any type ofsubstrate. Non-limiting examples include, paper, glass, ceramics, wood,masonry, textiles, metals and polymeric organic host materials.

[0488] The photochromic polyurethane coatings that can be used toprepare the photochromic coated articles of the present invention, inone non-limiting embodiment, can be produced by the catalyzed oruncatalyzed reaction of an organic polyol component and an isocyanatecomponent in the presence of photochromic compound(s). Materials andmethods for the preparation of polyurethanes are described in Ullmann'sEncyclopedia of Industrial Chemistry, Fifth Edition, 1992, Vol. A21,pages 665 to 716. Non-limiting examples of methods and materials, e.g.,organic polyols, isocyanates and other components, which can be used toprepare the polyurethane coating are disclosed in U.S. Pat. Nos.4,889,413 and 6,187,444B1.

[0489] The photochromic aminoplast resin coating composition that can beused to produce the photochromic coated articles of the presentinvention, in one non-limiting embodiment, can be prepared by combininga photochromic material with the reaction product of a functionalcomponent(s) having at least two functional groups chosen from hydroxyl,carbamate, urea or a mixture thereof and an aminoplast resin, e.g.,crosslinking agent as described in U.S. Pat. Nos. 4,756,973, 6,432,544B1and 6,506,488.

[0490] Photochromic polysilane coating compositions contemplated for usein preparing the photochromic coated articles of the present invention,in one non-limiting embodiment, are prepared by hydrolyzing at least onesilane monomer such as glycidoxypropyltrimethoxysilane,vinyltrimethoxysilane, methacryloxypropyltrimethoxysilane,tetramethoxysilane, tetraethoxysilane and/or methyltrimethoxysilane andcombining the hydrolyzate with at least one photochromic material asdescribed in U.S. Pat. No. 4,556,605.

[0491] Photochromic poly(meth)acrylate coating compositions contemplatedfor use in preparing the photochromic coated articles of the presentinvention can be prepared, in one non-limiting embodiment, by combiningphotochromic compound(s) with mono-, di- or multi-functional(meth)acrylates as described in U.S. Pat. Nos. 6,025,026 and 6,150,430and WO publication 01/02449 A2.

[0492] The polyanhydride photochromic coating composition that can beused to prepare the photochromic coated articles of the presentinvention can be prepared in one non-limiting embodiment, by thereaction of a hydroxyl-functional component and a polymericanhydride-functional component in a composition including at least oneorganic photochromic material as described in U.S. Pat. No. 6,432,544B1.Non-limiting examples of hydroxyl-functional components,anhydride-functional component(s) and other components that can be usedto prepare the polyanhydride photochromic coatings are disclosed in U.S.Pat. Nos. 4,798,745, 4,798,746 and 5,239,012.

[0493] Photochromic polyacrylamide coating compositions contemplated foruse in preparing the photochromic coated articles of the presentinvention, in one non-limiting embodiment, can be prepared by combininga photochromic component with the free radical initiated reactionproduct of a polymerizable ethylenically unsaturated compositioncomprising N-alkoxymethyl(meth)acrylamide and at least one othercopolymerizable ethylenically unsaturated monomer as described in U.S.Pat. No. 6,060,001. Methods for preparing N-alkoxymethyl(meth)acrylamidefunctional polymer are described in U.S. Pat. No. 5,618,586.

[0494] The photochromic epoxy resin coating compositions that can beused to prepare the photochromic coated articles of the presentinvention, in one non-limiting embodiment, can be prepared by combiningphotochromic compound(s), epoxy resins or polyepoxides and curing agentsas described in U.S. Pat. Nos. 4,756,973 and 6,268,055B1.

[0495] In another non-limiting embodiment, the types of photochromicpolymeric coatings comprising the film-forming polymers and the BWSphotochromic materials of the present invention with or without otherphotochromic compounds include paints, e.g., a pigmented liquid or pasteused for the decoration, protection and/or the identification of asubstrate; and inks, e.g., a pigmented liquid or paste used for writingand printing on substrates such as in producing verification marks onsecurity documents, e.g., documents such as banknotes, passport anddrivers' licenses, for which authentication or verification ofauthenticity may be desired.

[0496] Application of the polymeric coating can be by any of the methodsused in coating technology, non-limiting examples include, spraycoating, spin coating, spin and spray coating, spread coating, curtaincoating, dip coating, casting or roll-coating and methods used inpreparing overlays, such as the method of the type described in U.S.Pat. No. 4,873,029. The application method selected also depends on thethickness of the desired coating.

[0497] The thickness of the coatings on the photochromic articles of thepresent invention can vary widely. Coating having a thickness rangingfrom 1 to 50 microns can be applied by the methods used in coatingtechnology. Coating of a thickness greater than 50 microns can requirethe application of multiple coatings or molding methods typically usedfor overlays. In one non-limiting embodiment, the coating may range inthickness from 1 to 10,000 microns, e.g., from 5 to 1000, e.g., from 8to 400, e.g., from 10 to 250 microns. The thickness of the polymericcoating can range between any combination of these values, inclusive ofthe recited range, e.g., a thickness of from 20 to 200 microns.

[0498] Following application of the polymeric coating to the surface ofthe substrate, in one non-limiting embodiment, the coating is at leastpartially cured. In another non-limiting embodiment, the methods usedfor curing the photochromic polymeric coating include the methods usedfor forming an at least partially cured polymer. Such methods includeradical polymerization, thermal polymerization, photopolymerization or acombination thereof. Additional non-limiting methods include irradiatingthe coated substrate or at least partially cured polymer with infrared,ultraviolet, gamma or electron radiation so as to initiate thepolymerization reaction of the polymerizable components. This can befollowed by a heating step.

[0499] In one non-limiting embodiment, if required and if appropriate,the surface of the substrate to be coated is cleaned prior to applyingthe photochromic polymeric coating to produce the photochromic articleof the present invention. This can be done for the purposes of cleaningand/or promoting adhesion of the coating. Effective treatment techniquesfor plastics and glass are known to those skilled in the art.

[0500] In some non-limiting embodiments, it may be necessary to apply aprimer to the surface of the substrate before application of thephotochromic polymeric coating. The primer can serve as a barriercoating to prevent interaction of the coating ingredients with thesubstrate and vice versa, and/or as an adhesive layer to adhere thephotochromic polymeric coating to the substrate. Application of theprimer can be by any of the methods used in coating technology such as,for example, spray coating, spin coating, spin and spray coating, spreadcoating, dip coating, casting or roll-coating.

[0501] The use of protective coatings, some of which can containpolymer-forming organosilanes, as primers to improve adhesion ofsubsequently applied coatings has been described in U.S. Pat. No.6,150,430, which disclosure is incorporated herein by reference. In onenon-limiting embodiment, non-tintable coatings are used. Non-limitingexamples of commercial coating products include SILVUE® 124 and HI-GARD®coatings, available from SDC Coatings, Inc. and PPG Industries, Inc.,respectively. In addition, depending on the intended use of the coatedarticle, in one non-limiting embodiment, it can be necessary to apply anappropriate protective coating(s), such as an abrasion resistant coatingand/or coatings that can serve as oxygen barriers, onto the exposedsurface of the coating composition to prevent scratches from the effectsof friction and abrasion and interactions of oxygen with thephotochromic materials, respectively.

[0502] In some cases, the primer and protective coatings areinterchangeable, e.g., the same coating can be used as the primer andthe protective coating(s). Non-limiting examples of hardcoats includethose based on inorganic materials such as silica, titania and/orzirconia as well as organic hardcoats of the type that are ultravioletlight curable.

[0503] In one non-limiting embodiment, such protective coatings can beapplied to the surface of photochromic articles comprising at leastpartially cured polymers containing photochromic materials.

[0504] In another non-limiting embodiment, the article of the presentinvention comprises a substrate to which a primer is applied followed bythe photochromic polymeric coating and a protective hardcoat. In afurther non-limiting embodiment, the protective hardcoat is anorganosilane hardcoat.

[0505] In additional non-limiting embodiments, other coatings or surfacetreatments, e.g., a tintable coating, antireflective surface, etc., canalso be, applied to the photochromic articles of the present invention.An antireflective coating, e.g., a monolayer or multilayer of metaloxides, metal fluorides, or other such materials, can be deposited ontothe photochromic articles, e.g., lenses, of the present inventionthrough vacuum evaporation, sputtering, or some other method.

[0506] In a further non-limiting embodiment, the photochromic articlecomprising an at least partially cured polymer and at least one BWSmaterial with or without other photochromic material further comprises asuperstrate, e.g., a film or sheet comprising at least one organicpolymeric material. The photochromic material can be located in thesuperstrate, the at least partially cured polymer or both. The organicpolymeric material of the superstrate is the same as the organicpolymeric material described hereinafter as the substrate or hostmaterial. Non-limiting examples of the organic polymeric materialsinclude thermosetting or thermoplastic materials, for example athermoplastic polyurethane superstrate.

[0507] In a still further non-limiting embodiment, the superstrate canbe connected to the polymer surface directly, but does not becomethermally fused to the substrate. In another non-limiting embodiment,the superstrate can be adheringly bonded to the substrate by becomingthermally fused with the subsurface of the substrate. General conditionsunder which superstrates are adheringly bonded to a substrate are knownto those skilled in the art. Non-limiting conditions for adheringlylaminating a superstrate to a substrate include heating to a temperatureof from 250-350° F. (121- 177° C.) and applying pressure of from 150 to400 pounds per square inch (psi) (1034 to 2758 kPa). Sub-atmosphericpressures, e.g., a vacuum, can also be applied to draw down and conformthe superstrate to the shape of the substrate as known to those skilledin the art. Non-limiting examples include applying at a sub-atmosphericpressure within the range of from 0.001 mm Hg to 20 mm Hg (0.13 Pa to2.7 kPa).

[0508] After a laminate comprising a superstrate applied to as least onesurface of a substrate is formed, it can further comprise a protectivecoating or film superposed onto the superstrate. Such a protectivecoating or film, in one non-limiting embodiment, serves as an at leastpartially abrasion resistant coating or film. Non-limiting types ofprotective coatings include the aforedescribed hardcoats that arecurable by ultraviolet radiation and/or that contain organosilanes. Thethickness of the protective coating can vary widely and include theaforementioned range for the photochromic polymeric coatings.Non-limiting types of protective films include those made of organicpolymeric materials such as thermosetting and thermoplastic materials.In another non-limiting embodiment, the protective film is athermoplastic film made of polycarbonate. The thickness of theprotective film or sheet can vary widely. Typically, such films have athickness of from 1 to 20 mils (0.025 to 0.5 mm).

[0509] The host material for the BWS photochromic materials with orwithout other photochromic materials will usually be transparent, butmay be translucent or even opaque. The host material need only bepervious to that portion of the electromagnetic spectrum, whichactivates the photochromic material, e.g., that wavelength ofultraviolet (UV) light that produces the open or colored form of thephotochromic and that portion of the visible spectrum that includes theabsorption maximum wavelength of the photochromic in its UV activatedform, e.g., the open form. In one contemplated non-limiting embodiment,the host color should not be such that it masks the color of theactivated form of the photochromic materials, e.g., so the change incolor is readily apparent to the observer. Compatible tints may beapplied to the host material as described in U.S. Pat. No. 5,645,767 incolumn 13, line 59 to column 14, line 3.

[0510] In one contemplated non-limiting embodiment, the polymericorganic host material can be a solid transparent or optically clearmaterial, e.g., materials having a luminous transmittance of at least 70percent and are suitable for optical applications, such as opticalelements chosen from plano and ophthalmic lenses, ocular devices such asophthalmic devices that physically reside in or on the eye, e.g.,contact lenses and intraocular lenses, windows, automotivetransparencies, e.g., windshields, aircraft transparencies, plasticsheeting, polymeric films, etc.

[0511] Non-limiting examples of polymeric organic materials which can beused as a host material for the BWS photochromic materials of thepresent invention with or without other photochromic materials or as asubstrate for the photochromic polymeric coating include:poly(meth)acrylates, polyurethanes, polythiourethanes, thermoplasticpolycarbonates, polyesters, poly(ethylene terephthalate), polystyrene,poly(alpha methylstyrene), copoly(styrene-methyl methacrylate),copoly(styrene-acrylonitrile), polyvinylbutyral, poly(vinyl acetate),cellulose acetate, cellulose propionate, cellulose butyrate, celluloseacetate butyrate, polystyrene or polymers, such as homopolymers andcopolymers prepared by polymerizing monomers chosen from bis(allylcarbonate) monomers, styrene monomers, diisopropenyl benzene monomers,vinylbenzene monomers, e.g., those described in U.S. Pat. No. 5,475,074,diallylidene pentaerythritol monomers, polyol (allyl carbonate)monomers, e.g., diethylene glycol bis(allyl carbonate), vinyl acetatemonomers, acrylonitrile monomers, mono- or polyfunctional, e.g., di- ormulti-functional, (meth)acrylate monomers such as (C₁-C₁₂)alkyl(meth)acrylates, e.g., methyl (meth)acrylate, ethyl (meth)acrylate,butyl (meth)acrylate etc., poly(oxyalkylene)(meth)acrylate,poly(alkoxylated phenol (meth)acrylates), diethylene glycol(meth)acrylates, ethoxylated bisphenol A (meth)acrylates, ethyleneglycol (meth)acrylates, poly(ethylene glycol) (meth)acrylates,ethoxylated phenol (meth)acrylates, alkoxylated polyhydric alcohol(meth)acrylates, e.g., ethoxylated trimethylol propane triacrylatemonomers, urethane (meth)acrylate monomers, such as those described inU.S. Pat. No. 5,373,033, or a mixture thereof. Further examples ofpolymeric organic host materials are disclosed in the U.S. Pat. No.5,753,146, column 8, line 62 to column 10, line 34.

[0512] In another non-limiting embodiment, transparent copolymers andblends of transparent polymers are also suitable as polymeric materials.The host material can be an optically clear polymerized organic materialprepared from a thermoplastic polycarbonate resin, such as thecarbonate-linked resin derived from bisphenol A and phosgene, which issold under the trademark, LEXAN; a polyester, such as the material soldunder the trademark, MYLAR; a poly(methyl methacrylate), such as thematerial sold under the trademark, PLEXIGLAS; polymerizates of apolyol(allyl carbonate) monomer, especially diethylene glycol bis(allylcarbonate), which monomer is sold under the trademark CR-39, andpolymerizates of copolymers of a polyol (allyl carbonate), e.g.,diethylene glycol bis(allyl carbonate), with other copolymerizablemonomeric materials, and copolymers with a polyurethane having terminaldiacrylate functionality, as described in U.S. Pat. Nos. 4,360,653 and4,994,208; and copolymers with aliphatic urethanes, the terminal portionof which contain allyl or acrylyl functional groups, as described inU.S. Pat. No. 5,200,483.

[0513] A further non-limiting embodiment is use of the BWS materials ofthe present invention and other photochromic materials with opticalorganic resin monomers used to produce optically clear coatings, filmsand polymerizates, e.g., materials suitable for optical applications,such as for example plano and ophthalmic lenses, windows, and automotivetransparencies. Examples of non-limiting embodiments includepolymerizates of optical resins sold by PPG Industries, Inc. as TRIVEXmonomers and under the CR-designation, e.g., CR-307, CR-407 and CR-607and the resins used to prepare hard or soft contact lenses. Methods forproducing both types of contact lenses are disclosed in U.S. Pat. No.5,166,345, column 11, line 52, to column 12, line 52.

[0514] Further non-limiting embodiments of optical resins include theresins used to form soft contact lenses with high moisture contentdescribed in U.S. Pat. No. 5,965,630 and extended wear contact lensesdescribed in U.S. Pat. No. 5,965,631.

[0515] The present invention is more particularly described in thefollowing examples, which are intended as illustrative only, sincenumerous modifications and variations therein will be apparent to thoseskilled in the art.

[0516] The following photochromic materials (PM) were used in theexamples described hereinafter. PM-A through PM-P represent BWSmaterials and PM-AA and PM-BB represent other photochromic materials.PM-A 7,7-diphenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran PM-B7-phenyl-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran PM-C3,3-di(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2- b]pyran PM-D3-(4-morpholinophenyl)-3-phenyl-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2- b]pyran PM-E7-(2-fluorophenyl)-7-(3-methyl-4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho [1,2-b]pyran PM-F3-(4-methoxyphenyl)-3-phenyl-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2- b]pyran PM-G2-(4-methoxyphenyl)-2-(2,4-dimethoxyphenyl)-7-diphenylmethyl-10-methyl-5-oxo-2H-5H-pyrano[3′,4′:3,4]naphtho[1,2-b]pyran PM-H7-(4-methoxyphenyl)-7-(2,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4] naphtho[1,2-b]pyran PM-I7-(4-morpholino-2-fluorophenyl)-7-(4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran PM-J7-(2-fluoro-4-methoxyphenyl)-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran PM-K7-(4-morpholino-2-fluorophenyl)-7-(3,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran PM-L3-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4] naphtho[1,2-b]pyranPM-M 3,3-di(2-methoxyethoxyphenyl-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2- b]pyran PM-N3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4] naphtho[1,2-b]pyranPM-O 3,3-di(4-methoxyphenyl)-6,11-dimethoxy-13-butyl-13-ethoxy-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran PM-P3,3-di(4-methoxyphenyl)-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2- b]pyran PM-AA Anaphtho[1,2-b]pyran that exhibits a purple color when irradiated withultraviolet light. PM-BB A naphtho[1,2-b]pyran that exhibits ayellow-green color when irradiated with ultraviolet light.

EXAMPLE 1

[0517] The following materials were added in the order and the mannerdescribed to a container suitable for use with a BRINKMAN PT-3000homogenized: Charge 1 Material Weight (grams) 2-Ethoxyethyl ether 50.0Tetrahydrofurfuryl alcohol 30.0 m-Methyl pyrrolidone 20.0 Hydroxylpropylcellulose 12.0 Silica 0.9

[0518] Charge 2 Material Weight Percent PM-D/PM-E/PM-B in 45/45/10weight 1.65 ratio TINUVIN ® 144 UV Stabilizer⁽¹⁾ 0.83

[0519] Charge 1 was added to the container and mixed by the homogenizerat a speed of 5000 rpm for 2 minutes or until the materials weredissolved. Charge 2 was added to the container and the resulting mixturewas heated while mixing until the materials dissolved.

EXAMPLE 2

[0520] The procedure of Example 1 was followed except that in Charge 2the following combination of photochromic materials was used:PM-A/PM-C/PM-D/PM-E/PM-G/PM-P in a weight ratio of 15/15/15/5/40/10.

EXAMPLE 3

[0521] The procedure of Example 1 was followed except that in Charge 2the following combination of photochromic materials was used:PM-A/PM-B/PM-C/PM-D/PM-H in a weight ratio of 10/20/20/30/20.

EXAMPLE 4

[0522] The procedure of Example 1 was followed except that in Charge 2the following combination of photochromic materials was used:PM-A/PM-C/PM-I in a weight ratio of 25/45/30.

EXAMPLE 5

[0523] The procedure of Example 1 was followed except that in Charge 2the following combination of photochromic materials was used:PM-A/PM-C/PM-D/PM-E/PM-F in a weight ratio of 10/15/25/15/20.

EXAMPLE 6

[0524] The procedure of Example 1 was followed except that in Charge 2the following combination of photochromic materials was used:PM-A/PM-C/PM-D/PM-I/PM-J in a weight ratio of 30/24/20/13/13.

EXAMPLE 7

[0525] The procedure of Example 1 was followed except that in Charge 2the following photochromic material was used: PM-L.

EXAMPLE 8

[0526] The procedure of Example 1 was followed except that in Charge 2the following photochromic material was used: PM-K.

EXAMPLE 9

[0527] The procedure of Example 1 was followed except that in Charge 2the following combination of photochromic materials:PM-A/PM-C/PM-K/PM-AA/PM-BB in a weight ratio of 24/45/25/2/4 and 0.033percent by weight, based on the total weight of Charges 1 and 2, of D&CViolet #2 (CAS #81-48-1) were used.

EXAMPLE 10

[0528] The procedure of Example 1 was followed except that in Charge 2the following photochromic material was used: PM-M.

EXAMPLE 11

[0529] The procedure of Example 1 was followed except that in Charge 2the following photochromic material was used: PM-N.

EXAMPLE 12

[0530] The procedure of Example 1 was followed except that in Charge 2the following combination of photochromic materials was used:PM-A/PM-C/PM-I/PM-O/PM-AA/PM-BB in a weight ratio of 24/42/25/3/2/4.

COMPARATIVE EXAMPLE 1

[0531] The weight of the paper representing the area beneath theabsorption spectrum for Dye A in FIG. 1 of U.S. Pat. No. 6,102,543 wasdetermined as follows. FIG. 1 was enlarged 200 percent on a photocopier.The 410 nm point on the horizontal axis was established by determiningthat 100 nm equaled 39 mm and by marking the axis about 3.9 mm to theright of the 400 nm point. The area on the enlarged figure beneath thespectrum from 380 nm to 700 nm was cut out and weighed on a MettlerXA1200 balance. This was the total area weight. The area on the enlargedfigure beneath the spectrum from 410 nm to 700 nm was cutout andweighed. This corresponded to the visible area weight. The weight of thearea beneath the spectrum from 380 to 410 nm was determined bysubtracting the visible area weight from the total area weight. The areaweight percent of the spectrum in the visible region was calculated bydividing the visible area weight by the total area weight andmultiplying by 100. The area weight percent of the spectrum in theultraviolet region was calculated by dividing the ultraviolet areaweight by the total area weight and multiplying by 100. The results arelisted in Table 3.

Comparative Example 2

[0532] The procedure of Comparative Example 1 was followed except thatthe weight of the paper representing the area beneath the absorptionspectrum for Dye B in FIG. 1 of U.S. Pat. No. 6,102,543 was determined.

COMPARATIVE EXAMPLE 3

[0533] The procedure of Comparative Example 1 was followed except thatthe weight of the paper representing the area beneath the absorptionspectrum for Dye C in FIG. 1 of U.S. Pat. No. 6,102,543 was determined.

COMPARATIVE EXAMPLES 4-8

[0534] The commercially available plastic lenses described and listedbelow were used as Comparative Examples (CE). Each lens was a plano typelens that reportedly activated to a grey or brown color as indicated.Each lens was tested in duplicate and the average of the result wasreported hereinafter in Table 1. CE # Lens Description Thickness 4ACorning SunSensors ® 1.8 mm (grey) 4B Corning SunSensors ® 1.8 mm(brown) 5A Hoya Hilux ® 2.0 mm (grey) 5B Hoya Hilux ® 2.0 mm (brown) 6ATransitions ® Next 2.0 mm Generations (grey) 6B Transitions ® Next 2.0mm Generations (brown) 7A Rodenstock ® ColorMatic 1.9 mm Extra (grey) 7BRodenstock ® ColorMatic 1.9 mm Extra (brown) 8A Transitions ® III 1.502.0 mm (grey) 8B Transitions ® III 1.50 2.0 mm (brown)

EXAMPLE 13

[0535] The Behind the Windshield Test and the Outdoor Test are describedherein. The preparation of samples is described in Part A, testing ofphotochromic performance is described in Part B, testing of percenttransmission is described in Part C and the spectra of representativeBWS photochromic materials compared to Comparative Examples 1-3 isdescribed in Part D.

Part A

[0536] Testing of Examples 1-12 was done with test samples preparedusing CR-607® monomer available from PPG Industries, Inc., with theaddition of 0.02 weight percent Cyasorb® UV 5411, an ultraviolet lightabsorber from CIBA Specialty Chemicals Corp. and 2.5 parts per hundredof resin (pph) of diisopropyl peroxydicarbonate, a thermal initiator.The initiator and UV absorber were dissolved in the monomer by mixingand then the monomer was poured into molds measuring 12 inches by 12inches by 0.08 inches (30.5 centimeters by 30.5 centimeters by 0.2centimeters). The molds were cured according to the following cycle.Hold for 6 hours at 36° C.; ramp up to 56° C. over 8 hours; after 2.0hours at 56° C., ramp up to 72° C.; after 8 hours, at 72° C. removesample and cool to 60° C. and demold.

[0537] Afterwards, the cured sheets were cut into two inch by two inchsquares (5.08 centimeters by 5.08 centimeters). The test squares werewashed with dishwashing detergent and water, rinsed with deionized waterand wiped with an acetone soaked tissue prior to the application of theexample solutions. The imbibition coating was applied to the testsamples by dispensing a quantity of imbibition coating on the testsample and spinning at about 1500 rpm for about four seconds to producea wet film-weight of 0.35 to 0.40 milligrams per lens. The resultingfilms were dried under an infrared light for about 20 minutes and placedin an oven at 135-140° C. for the times indicated in the followingtable. Afterward, the imbibed test samples were washed with soap andrinsed with water. Example # Time 1, 2 and 5 4 hours 3, 4, and 6-12 8hours

Part B

[0538] The photochromic imbibed test squares prepared in Part A weretested for photochromic response in the Outdoor Test and the Behind theWindshield Test as described herein on a Bench for MeasuringPhotochromics (BMP) optical bench made by Essilor, France.

[0539] The Behind the Windshield Test was used to determine the changein optical density (ΔOD) obtained by the sample when tested underconditions simulating photochromic lens response on a wearer inside anautomobile. It was determined that the amount of light energy availableto activate a photochromic lens on a wearer in an automobile was 0.75Watts/m² integrated between 380 and 420 nm and 1.7 Klux (kilolumens/m²)whereas, the amount of energy available in the Outdoor Test was 6.7Watts/m² (UVA) integrated between 315 and 380 nm and 50 Klux. TheOutdoor Test was used to determine the change in optical densityobtained by the sample when tested under conditions simulatingphotochromic lens response on a wearer outdoors.

[0540] Prior to testing on the optical bench, the photochromic testsquares were conditioned by activating and fading as describedhereinafter. The test squares were first exposed to 365 nanometerultraviolet light for about 10 minutes at a distance of about 14centimeters to activate the photochromic compounds. The UVA (315 to 380nm) irradiance at the sample was measured with a Licor Model Li-1800spectroradiometer and found to be 22.2 watts per square meter. Theactivated samples were then placed under a 500 watt, high intensityhalogen lamp for about 10 minutes at a distance of about 36 centimetersto bleach or inactivate the photochromic compounds. The illuminance atthe sample was measured with the Licor spectroradiometer and found to be21.4 Klux. The test squares were then kept covered for at least 1 hourprior to testing on an optical bench.

[0541] The BMP optical bench was fitted with two 150 watt Xenon arclamps. The light path from Lamp 1 was directed through a 3 mm SchottKG-2 band-pass filter and appropriate neutral density filters thatcontributed to the required UV and partial visible light irradiancelevel. The light path from the Lamp 2 was directed through a 3 mm SchottKG-2 band-pass filter, a 400 nm cutoff filter and neutral densityfilters in order to provide supplemental visible light illuminance. Forthe outdoor test conditions, both lamps were used, but for the inautomobile simulation, only Lamp 1 with a direct irradiance path to thesample was used. In this irradiance path, the 3 mm Schott KG-2 band-passfilter and a simulated windshield typical of an auto windshield wereused to control the irradiance spectral profile. Neutral density filtersand voltage control of the Xenon arc lamp were used to adjust theintensity of the light.

[0542] The irradiance used for the Behind the Windshield Test wasdetermined to be an average radiant flux integrated between 380 and 420nm of 0.75 Watts/m² with 1.7 Klux of visible light. The samples werecontrolled at a temperature of 28° C. The outdoor simulated conditionswere an irradiance level of 6.7 Watts/m² UVA, 50 Klux and controlled ata temperature of 23° C. The simulated windshield was prepared bylaminating a 0.73 mm thick piece of polyvinylbutyrate film from SolutiaInc. between two 2.3 mm thick layers of Solex 97 glass from PPGIndustries, Inc. The simulated windshield had a total thickness of 5.33mm. A spectra of the light passing through the simulated windshield asmeasured on the BMP is shown in FIG. 1.

[0543] Proprietary software was used on the BMP to control timing,irradiance, air cell and sample temperature, shuttering, filterselection and response measurement. A Zeiss spectrophotometer, Model MCS501, with fiber optic cables for light delivery through the sample wasused for response and color measurement. For single photochromicsystems, response measurements were collected at the visible lambda max.Photopic response measurements were collected when testing multiplephotochromic lens systems.

[0544] Response measurements, in terms of change in optical density(ΔOD) from the unactivated state to the activated or darkened state weredetermined by establishing the initial unactivated transmittance,opening the shutter from the Xenon lamp(s) and measuring thetransmittance during activation of the sample at selected intervals oftime. Change in optical density was determined according to the formula:ΔOD=log(% Tb/% Ta), where % Tb is the percent transmittance in thebleached state, % Ta is the percent transmittance in the activated stateand the logarithm is to the base 10. Optical density measurement can beper specific wavelength or photopic.

[0545] The Percent of the ΔOD retained by the test samples wasdetermined by measuring the change in optical density (ΔOD) from thebleached to the darkened state under conditions corresponding to outdoorsimulation (OS) and behind the windshield (BWS) eyeglass wearersimulation. The examples of the present invention and comparativeexamples were activated until saturated which was 15 minutes for theexamples of the present invention and 30 minutes for the comparativeexamples. The measure used was the percent of ΔOD retained between thetwo conditions according to the following formula:

% ΔOD Retained=100×(ΔOD _(BWS)/ΔOD _(OS)).

[0546] Results for Examples 1-12 are in Table 1 and the results forComparative Examples 4A/4B to 8A/8B are in Table 1A. TABLE 1 ΔOD @ 15min. ΔOD @ 15 min. % ΔOD Example # (OS) 23° C. (BWS) 28° C. Retained 11.118 0.313 28 2 0.855 0.223 26 3 1.096 0.289 26 4 0.952 0.217 23 51.351 0.355 26 6 1.026 0.237 23 7 1.497 0.394 26 8 1.410 0.192 14 90.870 0.193 22 10 1.675 0.420 25 11 1.542 0.293 19 12 1.000 0.261 26

[0547] TABLE 1A ΔOD @ 30 min. ΔOD @ 30 min. % ΔOD Example # (OS) 23° C.(BWS) 28° C. Retained CE-4A 0.545 0.008 1.5 CE-4B 0.566 0.019 3.4 CE-5A0.537 0.056 10 CE-5B 0.478 0.054 11 CE-6A 0.786 0.080 10 CE-6B 0.7270.075 10 CE-7A 0.583 0.043 7.4 CE-7B 0.484 0.036 7.4 CE-8A 0.576 0.0406.9 CE-8B 0.484 0.040 8.3

[0548] The results of Table 1 show that Examples 1-12, when der behindthe windshield eyeglass wearer simulating conditions, retained from 14to 28 percent of the ΔOD measured under outdoor simulating conditions,whereas in Table 1A, Comparative Examples 4A/B to 8A/B retained lessthan 12 percent of the ΔOD measured under outdoor simulating conditions.

Part C

[0549] The photochromic test squares from Part A were conditioned byactivating and fading as described in Part B amd were tested for thepercent transmission through the sample unactivated bleached state underthe outdoor simulating (OS) condition of 23° C. and when activated underthe behind the windshield (BWS) eyeglass wearers simulating conditionsat 28° C. Testing was done using the BMP as described in Part B. Theresults are listed in Table 2. TABLE 2 Bleached State % Activated State% Transmission Transmission Example # (OS) 23° C. (BWS) 28° C. 1 82 39 286 52 3 84 44 4 82 44 5 85 39 6 82 48 7 84 45 8 77 59 9 76 49 10  86 4411  85 55 12  85 47 CE4A 85 83 CE4B 85 82 CE5A 87 76 CE5B 86 76 CE6A 8974 CE6B 89 75 CE7A 86 77 CE7B 85 78 CE8A 87 79 CE8B 88 80

[0550] The results of Table 2 show that Examples 1-12 demonstrate anactivated state luminous transmission at saturation of less than 60percent. Comparative Examples 4A/4B to 8A/8B demonstrated an activatedstate luminous transmission at saturation of greater than 60 percent.

Part D

[0551] The spectrum for each of Photochromic Materials: PM-A; PM-C;PM-D; PM-E; PM-F; PM-I and PM-J was prepared by dissolving enough ofeach photochromic material into a cuvette containing diethylene glycoldimethyl ether to result in a maximum absorbance of less than 1.0 asmeasured on a Cary Ultraviolet/Visible spectrophotometer, Model #3. Thefigure of absorbance versus wavelength for each photochromic materialwas printed at 100 percent. The 410 nm point on the horizontal axis wasestablished by determining that 20 nm equaled 6.0 mm and by marking thegraph 3.0 mm to the right of 400 nm. The paper representing the areabeneath the spectrum from 380 to 700 nm was cutout and weighed on aMettler XA1200 balance. This was the total area weight. The paperrepresenting the area beneath the spectrum between 380 and 410 nm wascutout and weighed. This corresponded to the UV area weight. The weightof the area beneath the spectrum from 410 to 700 nm was determined bysubtracting the ultraviolet area weight from the total area weight. Thearea weight percent of the spectrum in the UV region and visible regionwas calculated as done hereinbefore in Comparative Example 1. Theresults are listed in Table 3. TABLE 3 TOTAL Area UV VISIBLE Weight %Weight % from Area Area of of 380-700 from from UV Area VISIBLE nm380-410 nm 410-700 nm of Area of Weight Weight Weight TOTAL TOTALSpectra (mg) (mg) (mg) Area Area PM-A 30.2 27.7 2.5 92 8 PM-C 35.4 26.78.7 75 25 PM-D 35.4 25.2 10.2 71 29 PM-E 29.5 23.1 6.4 78 22 PM-F 28.523.0 5.5 81 19 PM-I 27.4 23.0 4.4 84 16 PM-J 29.3 24.5 4.8 84 16 PM-K28.6 22.8 5.8 80 20 CE-1 16.1 4.6 11.5 29 71 CE-2 27.1 7.1 20.0 26 74CE-3 71.0 6.6 64.4 9 91

[0552] The results of Table 3 show that each of the spectra ofPhotochromic Materials A, C, D, E, F, I, J and K had substantially morearea in the 380 to 410 nm ultraviolet wavelength range, than in the 410to 700 nm visible wavelength range. The results for the ComparativeExamples 1 through 3 showed substantially more area in the 410 to 700 nmvisible wavelength range than in the 380 to 410 nm ultravioletwavelength range.

[0553] The present invention has been described with reference tospecific details of particular embodiments thereof. It is not intendedthat such details be regarded as limitations upon the scope of theinvention except insofar as to the extent that they are included in theaccompanying claims.

We claim:
 1. A photochromic article comprising: a) a substrate; and b)at least one photochromic material adapted to change from an unactivatedform to an activated form by exposure to radiation substantially in thewavelength range from 380 to 410 nanometers when measured over a rangeof from 380 to 700 nanometers, said photochromic article being adaptedto retain at least 12 percent of the delta OD measured in the OutdoorTest when tested in the Behind the Windshield Test.
 2. The photochromicarticle of claim 1 wherein the photochromic article is adapted to retainat least 20 percent of the delta OD measured in the Outdoor Test whentested in the Behind the Windshield Test.
 3. The photochromic article ofclaim 1 wherein the photochromic article is adapted to retain at least25 percent of the delta OD measured in the Outdoor Test when tested inthe Behind the Windshield Test.
 4. The photochromic article of claim 1wherein photochromic material (b) is chosen from: (1) a photochromicmaterial chosen from a fluoranthenoxazine represented by the followinggraphic formula I:

wherein, (a) R₁ is chosen from hydrogen, C₁-C₈ alkyl, C₃-C₇cycloalkyl,phen(C₁-C₄)alkyl, naphth(C₁-C₄)alkyl, allyl, acrylyloxy(C₂-C₆)alkyl,methacrylyloxy(C₂-C₆)alkyl, C₂-C₄ acyloxy(C₂-C₆)alkyl,carboxy(C₂-C₆)alkyl, cyano(C₂-C₆)alkyl, hydroxy(C₂-C₆)alkyl,triarylsilyl, triarylsilyloxy, tri(C₁-C₆)alkylsilyl,tri(C₁-C₆)alkylsilyloxy, tri(C₁-C₆)alkoxysilyl,tri(C₁-C₆)alkoxysilyloxy, di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyl,di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyloxy, di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyl,di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyloxy, C₁-C₆ alkoxy(C₂-C₄)alkyl or(C₂H₄O)_(r).CH_(3,) wherein r is an integer from 1 to 6; (b) R₂ ischosen from C₁-C₅ alkyl, C₁-C₅ alkoxy, nitro, cyano, C₁-C₈alkoxycarbonyl, C₁-C₄ acyloxy, halo, C₁-C₄ monohaloalkyl or C₁-C₄polyhaloalkyl; said halo substituents being chloro, fluoro, iodo orbromo and q is 0, 1 or 2; (c) R₃ and R₄ are each independently chosenfrom C₁-C₅ alkyl, benzyl, phenyl, mono- or di-substituted phenyl, saidphenyl substituents being C₁-C₅ alkyl or C₁-C₅ alkoxy; or R₃ and R₄taken together form a group chosen from a cyclic ring of from 5 to 8carbon atoms which includes the spiro carbon atom; (d) R₅ is chosen fromhydrogen, —CH₂Q and —C(O)W, wherein Q is halogen, hydroxy, benzoyloxy,C₁-C₆ alkoxy, C₂-C₆ acyloxy, amino, C₁-C₆ mono-alkylamino, C₁-C₆dialkylamino, morpholino, piperidino, 1-indolinyl, pyrrolidyl,triarylsilyl, triarylsilyloxy, tri(C₁-C₆)alkylsilyl,tri(C₁-C₆)alkylsilyloxy, tri(C₁-C₆)alkoxysilyl,tri(C₁-C₆)alkoxysilyloxy, di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyl,di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyloxy, di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyl,di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyloxy, or the group, —OCH(R₈)Z; W is thegroup, —OCH(R₈)Z, or an unsubstituted, mono-substituted, ordi-substituted heterocyclic ring containing 5 to 6 ring atoms, whichring includes as the hetero atom a nitrogen atom alone or one additionalhetero atom of nitrogen or oxygen; wherein Z is —CN, —CF₃, halogen,—C(O)R₈, or —COOR₈, R₈ is hydrogen or C₁-C₆ alkyl; said heterocyclicring substituents being chosen from C₁-C₆ alkyl or C₁-C₆ alkoxy; or W is—OR₉ or —N(R₁₀)R₁₁, wherein R₉ is chosen from hydrogen, allyl, C₁-C₆alkyl, phenyl, mono(C₁-C₆)alkyl substituted phenyl,mono(C₁-C₆)alkoxy-substituted phenyl, phenyl(C₁-C₃)alkyl,mono(C₁-C₆)alkyl substituted phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxysubstituted phenyl(C₁-C₃)alkyl, C₁-C₆ alkoxy(C₂-C₄)alkyl, or C₁-C₆haloalkyl; and R₁₀ and R₁₁ are each independently chosen from hydrogen,C₁-C₆ alkyl, C₅-C₇ cycloalkyl, phenyl, mono- or di-substituted phenyl,or R₁₀ and R₁₁ together with the nitrogen atom form a mono- ordi-substituted or unsubstituted heterocyclic ring containing from 5 to 6ring atoms, which ring includes as the hetero atom said nitrogen atomalone or one additional hetero atom of nitrogen or oxygen, said phenyland heterocyclic ring substituents being C₁-C₆ alkyl or C₁-C₆ alkoxy,and each of said halogen or halo groups in this part (d) being fluoro orchloro; (e) each R₆ and R₇ is independently chosen for each occurrencefrom aryl, mono(C₁-C₆)alkoxyaryl, di(C₁-C₆)alkoxyaryl,mono(C₁-C₆)alkylaryl, di(C₁-C₆)alkylaryl, bromoaryl, chloroaryl,fluoroaryl, C₃-C₇ cycloalkylaryl, C₃-C₇ cycloalkyl, C₃-C₇ cycloalkyloxy,C₃-C₇ cycloalkyloxy(C₁-C₆)alkyl, C₃-C₇ cycloalkyloxy(C₁-C₆)alkoxy,aryl(C₁-C₆)alkyl, aryl(C₁-C₆)alkoxy, aryloxy, aryloxy(C₁-C₆)alkyl,aryloxy(C₁-C₆)alkoxy, mono- or di(C₁-C₆)alkylaryl(C₁-C₆)alkyl, mono- ordi(C₁-C₆)alkoxyaryl(C₁-C₆)alkyl, mono- ordi(C₁-C₆)alkylaryl(C₁-C₆)alkoxy, mono- ordi(C₁-C₆)alkoxyaryl(C₁-C₆)alkoxy, amino, mono(C₁-C₆)alkylamino,di(C₁-C₆)alkylamino, diarylamino, N-(C₁-C₆)alkylpiperazino,N-arylpiperazino, aziridino, indolino, piperidino, arylpiperidino,morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino,pyrryl, C₁-C₆ alkyl, C₁-C₆ bromoalkyl, C₁-C₆ chloroalkyl, C₁-C₆fluoroalkyl, C₁-C₆ alkoxy, mono(C₁-C₆)alkoxy(C_(l)-C₄)alkyl, acryloxy,methacryloxy, bromo, chloro or fluoro; and q is independently chosen foreach occurrence form the integer 0, 1, or 2; (2) a photochromic materialchosen from a naphthopyran represented by the following graphic formulaII:

wherein: (a) R₁₂ is hydrogen or a C₁-C₆ alkyl; (b) R₁₃ is hydrogen orthe group, —C(O)J, J being —OR₁₅ or —N(R₁₀)R₁₁, wherein R₁₅ is hydrogen,allyl, C₁-C₆ alkyl, phenyl, C₁-C₆ monoalkyl substituted phenyl, C₁-C₆monoalkoxy substituted phenyl, phenyl(C₁-C₃)alkyl, C₁-C₆ monoalkylsubstituted phenyl(C₁-C₃)alkyl, C₁-C₆ monoalkoxy substitutedphenyl(C₁-C₃)alkyl, C₁-C₆ alkoxy(C₂-C₄)alkyl, or C₁-C₆ monohaloalkyl,and wherein R₁₀ and R₁₁ are the same as described hereinbefore in (1)(d), and said halo substituent being chloro or fluoro; (c) R₁₄ is —OR₉,—N(R₁₀)R₁₁, wherein R₉, R₁₀ and R₁₁ are the same as describedhereinbefore in (1) (d), or the group, —C(O)V; wherein V is C₁-C₆ alkyl,phenyl, C₁-C₆ mono- or C₁-C₆ di-alkyl substituted phenyl, C₁-C₆ mono- orC₁-C₆ di-alkoxy substituted phenyl, C₁-C₆ alkoxy, phenoxy, C₁-C₆ mono-or C₁-C₆ di-alkyl substituted phenoxy, C₁-C₆ mono- or C₁-C₆ di-alkoxysubstituted phenoxy, C₁-C₆ alkylamino, phenylamino, C₁-C₆ mono- or C₁-C₆di-alkyl substituted phenylamino, or C₁-C₆ mono- or C₁-C₆ di-alkoxysubstituted phenylamino, and said halo substituent being chloro, fluoroor bromo, provided that either R₁₂ or R₁₃ is hydrogen; and (d) B and B′are each independently chosen from: (i) mono-T-substituted phenyl,wherein the group T is represented by the formula:—G[(OC₂H₄)_(x)(OC₃H₆)_(y)(OC₄H₈)_(z)]G′—[(OC₂H₄)_(x)(OC₃H₆)_(y)(OC₄H₈)_(z)]G′ wherein —G being chosen from —C(O)— or —CH₂—, G′ being chosen fromC₁-C₃ alkoxy or a polymerizable group, x, y and z each beingindependently chosen from a number between 0 and 50, and the sum of x, yand z being between 2 and 50; (ii) an unsubstituted, mono-, di-, ortri-substituted aryl group, phenyl or naphthyl; (iii) 9-julolidinyl orthe unsubstituted, mono- or di-substituted heteroaromatic group chosenfrom pyridyl furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl,benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl,carbazoyl, benzopyridyl, indolinyl or fluorenyl, each of said aryl andheteroaromatic substituents in (ii) and (iii) being independently chosenfrom hydroxy, —C(O)U, wherein U being hydroxy, C₁-C₆ alkyl, C₁-C₆alkoxy, phenyl, mono-substituted phenyl, amino, mono (C₁-C₆)alkylamino,di-(C₁-C₆)alkylamino, morpholino, piperidino or pyrrolidyl; aryl,mono(C₁-C₆)alkoxyaryl, di(C₁-C₆)alkoxyaryl, mono(C₁-C₆)alkylaryl,di(C₁-C₆)alkylaryl, chloroaryl, fluoroaryl, C₃-C₇ cycloalkylaryl, C₃-C₇cycloalkyl, C₃-C₇ cycloalkyloxy, C₃-C₇ cycloalkyloxy(C₁-C₆)alkyl, C₃-C₇cycloalkyloxy(C₁-C₆)alkoxy, aryl(C₁-C₆)alkyl, aryl(C₁-C₆)alkoxy,aryloxy, aryloxy(C₁-C₆)alkyl, aryloxy(C₁-C₆)alkoxy, mono- ordi-(C₁-C₆)alkylaryl(C₁-C₆)alkyl, mono- ordi-(C₁-C₆)alkoxyaryl(C₁-C₆)alkyl, mono- ordi-(C₁-C₆)alkylaryl(C₁-C₆)alkoxy, mono- ordi-(C₁-C₆)alkoxyaryl(C₁-C₆)alkoxy, amino, mono(C₁-C₆)alkylamino,di(C₁-C₆)alkylamino, diarylamino, piperazino, N-(C₁-C₆)alkylpiperazino,N-arylpiperazino, aziridino, indolino, piperidino, morpholino,thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl,C₁-C₆ alkyl, C₁-C₆ chloroalkyl, C₁-C₆ fluoroalkyl, C₁-C₆ alkoxy,mono(C₁-C₆)alkoxy(C₁-C₄)alkyl, acryloxy, methacryloxy, bromo, chloro orfluoro, said aryl being chosen from phenyl or naphthyl; (iv) anunsubstituted or mono-substituted group chosen from pyrazolyl,imidazolyl, pyrazolinyl, imidazolinyl, pyrrolinyl, phenothiazinyl,phenoxazinyl, phenazinyl or acridinyl, each of said substituents beingindependently chosen from C₁-C₆ alkyl, C₁-C₆ alkoxy, phenyl, fluoro,chloro or bromo; (v) a monosubstituted phenyl, said phenyl having asubstituent located at the para position being —(CH₂)_(r)— or—O—(CH₂)_(r)—, wherein r being chosen from the integer 1, 2, 3, 4, 5 or6, said substituent being connected to an aryl group which is a memberof another photochromic material, and; (vi) a group represented by oneof the following graphic formulae:

wherein A being independently chosen in each formula from methylene oroxygen and D being independently chosen in each formula from oxygen orsubstituted nitrogen, provided that when D is substituted nitrogen, A ismethylene; said nitrogen substituents being chosen from hydrogen, C₁-C₆alkyl, or C₂-C₆ acyl; each R₂₀ being independently chosen for eachoccurrence in each formula from C₁-C₆ alkyl, C₁-C₆ alkoxy, hydroxy,chloro or fluoro; R₁₈ and R₁₉ each being independently chosen in eachformula from hydrogen or C₁-C₆ alkyl; and q being chosen from theinteger 0, 1 or 2; (vii) C₁-C₆ alkyl, C₁-C₆ chloroalkyl, C₁-C₆fluoroalkyl, C₁-C₆ alkoxy(C₁-C₄)alkyl, C₃-C₆ cycloalkyl,mono(C₁-C₆)alkoxy(C₃-C₆)cycloalkyl, mono(C₁-C₆)alkyl(C₃-C₆)-cycloalkyl,chloro(C₃-C₆)cycloalkyl, fluoro(C₃-C₆)cyclo-alkyl or C₄-C₁₂bicycloalkyl; (viii) a group represented by the following graphicformula:

wherein L being chosen from hydrogen or C₁-C₄ alkyl and M being chosenfrom an unsubstituted, mono-, or di-substituted group chosen fromnaphthyl, phenyl, furanyl, or thienyl; each of said group substituentsbeing independently chosen from C₁-C₄ alkyl, C₁-C₄ alkoxy, fluoro, orchloro; or (ix) B and B′ taken together form fluoren-9-ylidene, mono-,or di-substituted fluoren-9-ylidene or a group being independentlychosen from saturated C₃-C₁₂spiro-monocyclic hydrocarbon rings,saturated C₇-C₁₂ spiro-bicyclic hydrocarbon rings or saturated C₇-C₁₂spiro-tricyclic hydrocarbon rings; each of said fluoren-9-ylidenesubstituents being independently chosen from C₁-C₄ alkyl, C₁-C₄ alkoxy,fluoro or chloro; (3) a photochromic material chosen from a naphthopyranrepresented by the following graphic formula III:

wherein, (a) R₂₁ is the group, —C(O)W or CH₂Q, described hereinbefore in(1) (d); (b) R₂₂ and each R₂₃ are independently chosen for eachoccurrence from hydroxy, NH₂ or N(R)H; wherein R is C₁-C₆ alkyl or aryland n is chosen from the integers 0, 1, 2, or 3; (c) B and B′ are eachindependently chosen from the groups described hereinbefore in (2) (d);(4) a photochromic material chosen from a naphthopyran represented bythe following graphic formula IV:

wherein, (a) R₅ is the same group described hereinbefore in (1) (d); (b)R₂₄ and R₂₅ are each chosen from hydrogen or an amino group definedhereinafter, provided that R₂₄ and R₂₅ are not both hydrogen; said aminogroup being: (i) —N(R₁₆)R₁₇, R₁₆ and R₁₇ each being independently chosenfrom hydrogen, C₁-C₈ alkyl, aryl, furanyl, benzofuran-2-yl,benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl,dibenzofuranyl, dibenzothienyl, benzopyridyl, fluorenyl, C₁-C₈alkylaryl, C₃-C₂₀ cycloalkyl, C₄-C₂₀ bicycloalkyl, C₅-C₂₀ tricycloalkylor C₁-C₂₀ alkoxyalkyl and said aryl group being phenyl or naphthyl; (ii)a nitrogen containing ring represented by the following graphic formula:

wherein each Y being independently chosen for each occurrence from—CH₂—, —CH(R₂₆)—, —C(R₂₆)(R₂₆)—, —CH(aryl)—, —C(aryl)₂— or—C(R₂₆)(aryl)—; X being —Y—, —O—, —S—, —S(O)—, —S(O₂)—, —NH—, —N(R₂₆)—or —N(aryl)—; R₂₆ being C₁-C₆ alkyl; said aryl group being phenyl ornaphthyl, m being chosen from the integer 1, 2 or 3 and p being chosenfrom the integer 0, 1, 2 or 3; provided that when p is 0, X is Y; (iii)a group represented by one of the following graphic formulae:

wherein each R₂₈, R₂₉ and R₃₀ being chosen independently for eachoccurrence in each formula from hydrogen, C₁-C₅ alkyl, phenyl ornaphthyl; or the groups R₂₈ and R₂₉ together form a ring of 5 to 8carbon atoms; R₂₇ being chosen independently for each occurrence fromC₁-C₆ alkyl, C₁-C₆ alkoxy, fluoro or chloro and q being chosen from theinteger 0, 1 or 2; (iv) unsubstituted, mono- or di-substituted C₄-C₁₈spirobicyclic amine; or (v) unsubstituted, mono- or di-substitutedC₄-C₁₈ spirotricyclic amine; said substituents for (iv) and (v) beingindependently chosen for each occurrence from aryl, C₁-C₆ alkyl, C₁-₆alkoxy or phenyl(C₁-C₆)alkyl; (c) B and B′ are each independently chosenfrom the groups described hereinbefore in (2) (d); (5) a photochromicmaterial chosen from a phenanthropyran represented by one of thefollowing graphic formula VA or VB:

wherein, (a) R₃₁ is the group R₅, described hereinbefore in (1) (d); (b)R₃₂ is hydrogen, C₁-C₆ alkyl, C₁-C₆ alkoxy, C₃-C₇ cycloalkyl, pyridyl,phenyl, mono-substituted or di-substituted phenyl, said phenylsubstituents being C₁-C₆ alkyl, C₁-C₆ alkoxy, hydroxy, amino, chloro, orfluoro; (c) each R₃₃ is independently chosen for each occurrence fromchloro, fluoro, amino, C₁-C₆ monoalkylamino, —N(R₁₀)R₁₁, which wasdescribed hereinbefore in (1) (d), phenyl, C₁-C₆ alkyl, or —OR₃₄,wherein R₃₄ is hydrogen, C₁-C₆ alkyl, allyl, or acetyl, and q is theinteger 0, 1, or 2; and (d) B and B′ are each independently chosen fromthe groups described hereinbefore in (2) (d); (6) a photochromicmaterial chosen from a fluoranthenopyran represented by the followinggraphic formula VI:

wherein, (a) R₃₅ and R₃₆ are each independently chosen for eachoccurrence from hydroxy, aryl, mono(C₁-C₆)alkoxyaryl,di(C₁-C₆)alkoxyaryl, mono(C₁-C₆)alkylaryl, di(C₁-C₆)alkylaryl,bromoaryl, chloroaryl, fluoroaryl, C₃-C₇ cycloalkylaryl, C₃-C₇cycloalkyl, C₃-C₇ cycloalkyloxy, C₃-C₇ cycloalkyloxy(C₁-C₆)alkyl, C₃-C₇cycloalkyloxy(C₁-C₆)alkoxy, aryl(C₁-C₆)alkyl, aryl(C₁-C₆)alkoxy,aryloxy, aryloxy(C₁-C₆)alkyl, aryloxy(C₁-C₆)alkoxy, mono- ordi(C₁-C₆)alkylaryl(C₁-C₆)alkyl, mono- anddi(C₁-C₆)alkoxyaryl(C₁-C₆)alkyl, mono- ordi(C₁-C₆)alkylaryl(C₁-C₆)alkoxy, mono- ordi(C₁-C₆)alkoxyaryl(C₁-C₆)alkoxy, C₁-C₆ alkyl, C₁-C₆ bromoalkyl, C₁-C₆chloroalkyl, C₁-C₆ fluoroalkyl, C₁-C₆ alkoxy,mono(C₁-C₆)alkoxy(C₁-C₄)alkyl, acryloxy, methacryloxy, bromo, chloro,fluoro, amino, mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, phenylamino,mono- or di-(C₁-C₆)alkyl substituted phenylamino or mono- ordi-(C₁-C₆)alkoxy substituted phenylamino, and q is the integer 0, 1 or2; (b) R₅ is chosen from the group described hereinbefore in (1) (d);and (c) B and B′ are each independently chosen from the groups describedhereinbefore in (2) (d); (7) a photochromic material chosen from anaphthopyran represented by the following graphic formula VII:

wherein, (a) R₃₇ and R₃₈ together form an oxo group or R₃₇ and R₃₈ eachare independently chosen for each occurrence from hydrogen, C₁-C₆ alkyl,C₃-C₇ cycloalkyl, allyl, phenyl, mono- or di-substituted phenyl, benzyl,mono-substituted benzyl, naphthyl, mono- or di-substituted naphthyl,C₄-C₁₂ bicycloalkyl, linear or branched C₃-C₁₂ alkenyl, C₁-C₆ alkoxycarbonyl(C₁-C₆)alkyl, methacryloxy(C₁-C₆)alkyl, acryloxy(C₁-C₆)alkyl,C₁-C₄ acyloxy(C₁-C₆)alkyl, C₁-C₆ alkoxy(C₁-C₆)alkyl or theunsubstituted, mono- or di-substituted heteroaromatic groups pyridyl,furanyl, benzofuran-2-yl, benzyfuran-3-yl, thienyl, benzothien-2-yl,benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazolyl,benzopyridyl and indolyl, each of said phenyl, benzyl, naphthyl andheteroaromatic group substituents being C₁-C₆ alkyl, C₁-C₆ alkoxy,morpholino, di(C₁-C₆)alkylamino, chloro or fluoro; (b) R₃₉ is chosenfrom C₁-C₆ alkyl, C₁-C₆ alkoxy, chloro, fluoro, phenyl, mono- anddi-substituted phenyl, benzyl or mono-substituted benzyl, C₃-C₇cycloalkyl, aryloxy, di(C₁-C₆)alkylamino, morpholino, thiomorpholino,piperidino, pyridyl, tetrahydroquinolino, isoquinolino, aziridino,diarylamino, N-(C₁-C₆)alkyl piperizino or N-aryl piperizino, wherein thearyl groups are phenyl or naphthyl, each of said phenyl and benzylsubstituents being C₁-C₆ alkyl, C₁-C₆ alkoxy, fluoro or chloro, and q isthe integer 0, 1 or 2; (c) I is oxygen or —N(R₄₀)—, wherein R₄₀ ishydrogen, C₁-C₆ alkyl, C₃-C₇ cycloalkyl, allyl, vinyl, C₁-C₅ acyl,phenyl, mono- or di-substituted phenyl, benzyl, mono-substituted benzyl,C₁-C₄ alkoxycarbonyl(C₁-C₆)alkyl, methacryloxy(C₁-C₆)alkyl,acryloyloxy(C₁-C₆)alkyl, phenyl(C₁-C₆)alkyl, naphthyl, C₄-C₁₂bicycloalkyl, C₂-C₄ acyloxy or the unsubstituted or substitutedheteroaromatic groups pyridyl, furanyl, benzofuran-2-yl,benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl,dibenzofuranyl, dibenzothienyl, carbazolyl, benzopyridyl or indolyl,each of said phenyl, benzyl and heteroaromatic group substituents beingC₁-C₆ alkyl or C₁-C₆ alkoxy; (d) K is oxygen, —N(R₄₀)— or —C(R₄₁)(R₄₂)—,wherein R₄₁ and R₄₂ are each hydrogen, C₁-C₆ alkyl or C₃-C₇ cycloalkyl;and (e) B and B′ are each independently chosen from the groups describedhereinbefore in (2) (d); (8) a photochromic material chosen from anaphthopyran represented by the following graphic formula VIII:

wherein, (a) R₄₃ and R₄₄ together form an oxo group or R₄₃ and R₄₄ areboth hydrogen, C₁-C₆ alkyl, C₃-C₇ cycloalkyl, allyl, phenyl,mono-substituted phenyl, benzyl or mono-substituted benzyl each of saidphenyl and benzyl group substituents being C₁-C₆ alkyl or C₁-C₆ alkoxy;(b) R₄₅ is hydrogen, C₁-C₆ alkyl, C₃-C₇ cycloalkyl, or the group,CH(B)B′, wherein B and B′ are each independently chosen from the groupsdescribed hereinbefore in (2) (d); (c) R₄₆ is hydrogen, C₁-C₆ alkyl, orC₃-C₇ cycloalkyl; (d) each R₄₇ is C₁-C₆ alkyl, C₁-C₆ alkoxy, chloro orfluoro, and q is the integer 0, 1, or 2; and (e) B and B′ are eachindependently chosen from the groups described hereinbefore in (2) (d);(9) a photochromic material chosen from a naphthopyran represented bythe following graphic formulae IXA, IXB, IXC, IXD, IXE, IXF, IXG or IXH:

wherein, (a) R₄₃ and R₄₄ are the same groups described hereinbefore in(8) (a); (b) each R₄₇ and q are the same as described hereinbefore in(8) (d); and (c) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (2) (d); (10) a photochromic material chosenfrom a naphthopyran represented by the following graphic formulae XA orXB:

wherein, (a) A′ is chosen from: (i) an unsubstituted, mono-substitutedor di-substituted heterocyclic ring chosen from benzothieno, benzofuranoor indolo, the 2,3 or 3,2 positions of said heterocyclic ring beingfused to the i, j or k side of said naphthopyran represented by graphicformula XA or said heterocyclic ring is fused to the f side of saidnaphthopyran represented by graphic formula XB; or (ii) anunsubstituted, mono-substituted or di-substituted indeno group fused tothe i, j or k side of said naphthopyran represented by graphic formulaXA or to the f side of said naphthopyran represented by graphic formulaXB; each of said heterocyclic ring and indeno group substituents beingC₁-C₆ alkyl, C₅-C₇ cycloalkyl, C₁-C₆ alkoxy, —N(R₁₀)R₁₁, which wasdescribed hereinbefore in (1) (d), chloro, fluoro, benzo, mono- ordi-substituted benzo group fused to the benzo portion of thebenzothieno, benzofurano, indeno or indolo moiety, said benzosubstitutent being C₁-C₆ alkyl, C₅-C₇ cycloalkyl, C₁-C₆ alkylmono-substituted (C₅-C₇)cycloalkyl, C₁-C₆ alkoxy, —N(R₁₀)R₁₁, which wasdescribed hereinbefore in (1) (d), chloro or fluoro; (b) R₄₈ is chosenfrom: (i) —C(O)W′, W′ being —OR₉ or —N(R₁₀)R₁₁, wherein said groups weredescribed hereinbefore in (1) (d); or (ii) —C(R₅₁)₂X′, wherein X′ is—CN, chloro, fluoro, hydroxy, benzoyloxy, C₁-C₆ alkoxy, C₂-C₆ acyloxy,amino, C₁-C₆ mono-alkylamino, C₁-C₆ dialkylamino, morpholino,piperidino, 1-indolinyl, pyrrolidyl, or trimethylsilyloxy, R₅₁ ishydrogen, C₁-C₆ alkyl, phenyl or naphthyl, and each of said phenyl andheterocyclic ring substituents in this part (b) (i) and (ii) being C₁-C₆alkyl or C₁-C₆ alkoxy; (c) R₄₉ is hydrogen, C₁-C₆ alkyl, the mono-, di-or tri-substituted aryl groups phenyl or naphthyl, said arylsubstituents being C₁-C₆ alkyl, C₁-C₆ alkoxy, chloro or fluoro; or (d)each R₅₀ is chloro, fluoro, C₁-C₆ alkyl, C₁-C₆ alkoxy, phenyl, naphthyl,phenoxy, naphthoxy or the group, —N(R₁₀)R₁₁, described hereinbefore in(1) (d), and q is selected from the integers 0, 1 or 2 in saidnaphthopyran represented by graphic XA, or each R₅₀ is chloro, fluoro,phenoxy, naphthoxy or the group, —N(R₁₀)R₁₁, and p is selected from theintegers 0, 1, 2 or 3 in said naphthopyran represented by graphicformula XB; and (e) B and B′ are each independently chosen from thegroups described hereinbefore in (2) (d); (11) a photochromic materialchosen from a indenonaphthopyran represented by the following graphicformulae XIA or XIB:

wherein, (a) A″ is an unsubstituted, mono-substituted or di-substitutedheterocyclic ring chosen from furo, thieno, benzothieno, benzofurano orindolo, the 2,3 or 3,2 positions of said heterocyclic ring being fusedto the g, h or i side of XIB or to the n, o or p side of XIA, saidheterocyclic ring substituents being C₁-C₆ alkyl, C₅-C₇ cycloalkyl,C₁-C₆ alkoxy, chloro or fluoro; (b) R₅₂ and R₅₃ together form an oxogroup, a spiro heterocyclic group having 2 oxygen atoms and from 3 to 6carbon atoms including the spirocarbon atom, or R₅₂ and R₅₃ are eachhydrogen, hydroxy, C₁-C₆ alkyl, C₃-C₇cycloalkyl, allyl, phenyl,mono-substituted phenyl, benzyl, mono-substituted benzyl, chloro, fluoroor the group, —C(O)W″, wherein each W″ is hydroxy, C₁-C₆ alkyl, C₁-C₆alkoxy, phenyl, mono-substituted phenyl, amino, mono(C₁-C₆)alkylamino,di(C₁-C₆)alkylamino, morpholino, piperidino or pyrrolidyl; or R₅₂ andR₅₃ are each the group, the group, —N(R₁₀)R₁₁, described hereinbefore in(1) (d), or —OR₅₄, wherein each R₅₄ is C₁-C₆ alkyl, phenyl(C₁-C₃)alkyl,mono(C₁-C₆)alkyl substituted phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxysubstituted phenyl(C₁-C₃)alkyl, C₁-C₆ alkoxy(C₂-C₄)alkyl, C₃-C₇cycloalkyl, mono(C₁-C₄)alkyl substituted C₃-C₇ cycloalkyl, C₁-C₆chloroalkyl, C₁-C₆ fluoroalkyl, allyl, the group, —CH(R₅₅)X″, whereineach R₅₅ is hydrogen or C₁-C₃ alkyl, each X″ is —CN, —CF₃, or —COOR₅₅,or each R₅₄ is the group, —C(O)Y″, wherein each Y′ is hydrogen, C₁-C₆alkyl, C₁-C₆ alkoxy, the unsubstituted, mono- or di-substituted arylgroups, phenyl or naphthyl, phenoxy, mono- or di-(C₁-C₆)alkylsubstituted phenoxy, mono- or di-(C₁-C₆)alkoxy substituted phenoxy,amino, mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, phenylamino, mono- ordi-(C₁-C₆)alkyl substituted phenylamino or mono- or di-(C₁-C₆)alkoxysubstituted phenylamino, each of said phenyl, benzyl or aryl groupsubstituents being C₁-C₆ alkyl or C₁-C₆ alkoxy; (c) each R₄₇ and q arethe same as described hereinbefore in (8) (d); and (d) B and B′ are eachindependently chosen from the groups described hereinbefore in (2) (d);(12) a photochromic material chosen from an indenonaphthopyranrepresented by graphic formulae XIIA or XIIB wherein:

(a) A″ is the same group as described hereinbefore in (11) (a) whereinA″ is fused to the g, h or i side of XIIB or to the n, o or p side ofXIIA,; (b) R₅₆ is hydrogen, hydroxy, bromo, fluoro or chloro and R₅₇ isthe group, —CH(V′)₂, wherein V′ is —CN or —COOR₅₈, and each R₅₈ ishydrogen, C₁-C₆ alkyl, phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkyl substitutedphenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl orthe unsubstituted, mono- or di-substituted aryl groups phenyl ornaphthyl, or R₅₇ is the group, —CH(R₅₉)Y″, wherein R₅₉ is hydrogen,C₁-C₆ alkyl or the unsubstituted, mono- or di-substituted aryl groupsphenyl or naphthyl, and Y″ is —COOR₅₈, —COR₅₉, or —CH₂OR₆₀, wherein R₅₉is hydrogen, C₁-C₆ alkyl, the unsubstituted, mono- or di-substitutedaryl groups phenyl or naphthyl, amino, mono(C₁-C₆)alkylamino,di(C₁-C₆)alkylamino, phenylamino, mono-or di-(C₁-C₆)alkyl substitutedphenylamino, mono- or di-(C₁-C₆)alkoxy substituted phenylamino,diphenylamino, mono- or di-(C₁-C₆)alkyl substituted diphenylamino, mono-or di-(C₁-C₆)alkoxy substituted diphenylamino, morpholino, orpiperidino; R₆₀ is hydrogen, —COR₅₈, C₁-C₆ alkyl, C₁-C₃alkoxy(C₁-C₆)alkyl, phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkyl substitutedphenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl, orthe unsubstituted, mono- or di-substituted aryl groups phenyl ornaphthyl, each of said aryl group substituents being C₁-C₆ alkyl orC₁-C₆ alkoxy; or (c) R₅₆ and R₅₇ together form the group, ═C(V′)₂ or═C(R₅₉)W′″, wherein W′″ is —COOR₅₈ or —COR₅₉; (d) each R₄₇ and q are thesame as described hereinbefore in (8) (d); and (e) B and B′ are eachindependently chosen from the groups described hereinbefore in (2) (d);(13) a photochromic material chosen from an indenonaphthopyranrepresented by the following graphic formula XIII:

wherein, (a) R₆₁ is represented by: (i) —SR₆₇, R₆₇ being chosen fromC₁-C₆ alkyl, aryl, mono- or di-substituted aryl, said aryl group beingphenyl or naphthyl and each of said aryl substitutents being chosenindependently from C₁-C₆ alkyl, C₁-C₆ alkoxy or halogen; (ii) an aminogroup described hereinbefore in (4) (b) (i), (ii), (iii), (iv) or (v);(b) R₆₁′ is independently chosen for each occurrence from C₁-C₆ alkyl orC₁-C₆ alkoxy and q being chosen from the integer 0, 1 or 2; (c) R₆₂ andR₆₃ are each independently chosen from: (i) hydrogen, hydroxy, amino,mono- or di-substituted amino, C₁-C₂ alkyl, C₃-C₁₂ alkylidene, C₂-C₁₂alkylidyne, vinyl, C₃-C₇ cycloalkyl, C₁-C₆ alkoxyalkyl, allyl, benzyl,mono-substituted benzyl, chloro, fluoro or —C(O)W″, wherein W″ being thesame group described hereinbefore in (11) (b); said amino substituentsin (c) (i) being C₁-C₆ alkyl, phenyl, benzyl or naphthyl; each of saidbenzyl substituents being C₁-C₆ alkyl or C₁-C₆ alkoxy; (ii) anunsubstituted, mono- di- or tri-substituted group chosen from phenyl,naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl,thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl orindolyl; each of said group substituents in (c) (ii) being chosenindependently for each occurrence from chloro, fluoro, C₁-C₆ alkyl orC₁-C₆ alkoxy; (iii) a monosubstituted phenyl, said phenyl having asubstituent located at the para position being as described hereinbeforein (2) (d) (v); (iv) —OR₆₇, R₆₇ being chosen from C₁-C₆ alkyl, C₁-C₆acyl, phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkyl substitutedphenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl,C₁-C₆ alkoxy(C₂-C₄)alkyl, C₃-C₇ cycloalkyl, mono(C₁-C₄)alkyl substitutedC₃-C₇ cycloalkyl, C₁-C₆ chloroalkyl, C₁-C₆ fluoroalkyl, allyl,triarylsilyl, triarylsilyloxy, tri(C₁-C₆)alkylsilyl,tri(C₁-C₆)alkylsilyloxy, tri(C₁-C₆)alkoxysilyl,tri(C₁-C₆)alkoxysilyloxy, di(C_(l)-C₆)alkyl(C₁-C₆ alkoxy)silyl,di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyloxy, di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyl,di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyloxy, benzoyl, mono-substituted benzoyl,naphthoyl or mono-substituted naphthoyl; each of said benzoyl andnaphthoyl substituents being independently chosen from C₁-C₆ alkyl orC₁-C₆ alkoxy; or R₆₇ being —CH(R₆₈)Q″, wherein R₆₈ being chosen fromhydrogen or C₁-C₃ alkyl and Q″ being chosen from —CN, —CF₃, or —COOR₆₈;or R₆₇ being —C(O)V″, wherein V″ being chosen from hydrogen, C₁-C₆alkoxy, phenoxy, mono- or di-(C₁-C₆)alkyl substituted phenoxy, mono- ordi-(C₁-C₆)alkoxy substituted phenoxy, an unsubstituted, mono- ordi-substituted aryl group, phenyl or naphthyl, amino,mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, phenylamino, mono- ordi-(C₁-C₆)alkyl substituted phenylamino, or mono- or di-(C₁-C₆)alkoxysubstituted phenylamino; each of said aryl group substituents beingindependently chosen from C₁-C₆ alkyl or C₁-C₆ alkoxy; (v) —CH(Q′″)₂,Q′″ being chosen from —CN or —COOR₆₉ and R₆₉ being chosen from hydrogen,C₁-C₆ alkyl, phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkyl substitutedphenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl; each of said aryl group substituents being independentlychosen from C₁-C₆ alkyl or C₁-C₆ alkoxy; (vi) —CH(R₇₀)G″, R₇₀ beingchosen from hydrogen, C₁-C₆ alkyl or an unsubstituted, mono- ordi-substituted aryl group, phenyl or naphthyl, and G″ being chosen from—COOR₆₉, —COR₇₁ or —CH₂OR₇₂, wherein R₇₁ being chosen from hydrogen,C₁-C₆ alkyl, an unsubstituted, mono- or di-substituted aryl group,phenyl or naphthyl, amino, mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino,phenylamino, mono- or di-(C₁-C₆)alkyl substituted phenylamino, mono- ordi-(C₁-C₆)alkoxy substituted phenylamino, diphenylamino, mono- ordi(C₁-C₆)alkyl substituted diphenylamino, mono- or di(C₁-C₆)alkoxysubstituted diphenylamino, morpholino or piperidino; R₇₂ being chosenfrom hydrogen, —C(O)R₆₉, C₁-C₆ alkyl, C₁-C₃ alkoxy(C₁-C₆)alkyl,phenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl oran unsubstituted, mono- or di-substituted aryl group, phenyl ornaphthyl, each of said aryl group substituents being independentlychosen from C₁-C₆ alkyl or C₁-C₆ alkoxy; (vii) the group T being thesame as described hereinbefore in (2) (d) (i); or (viii) R₆₂ and R₆₃together form an oxo group or a substituted or unsubstitutedspiro-carbocyclic ring containing 3 to 6 carbon atoms or a substitutedor unsubstituted spiro-heterocyclic group containing 1 or 2 oxygen atomsand 3 to 6 carbon atoms including the spirocarbon atom, saidspiro-carbocyclic ring and spiro-heterocyclic group being annellatedwith 0, 1 or 2 benzene rings, said substituents being hydrogen or C₁-C₆alkyl; (d) R₆₄ is chosen from hydrogen, C₁-C₆ alkyl or the group R_(a)chosen from: (i) —OR_(73,) R₇₃ being chosen from phenyl(C₁-C₃)alkyl,C₁-C₆ alkyl, mono(C₁-C₆)alkyl substituted phenyl(C₁-C₃)alkyl,mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl, C₁-C₆alkoxy(C₂₋C₄)alkyl, C₃-C₇ cycloalkyl, mono(C₁-C₄)alkyl substituted C₃-C₇cycloalkyl, C₁-C₆ chloroalkyl, C₁-C₆ fluoroalkyl, allyl or —CH(R₆₈)Q″described in (c) (i); or (ii) an amino group being the same describedhereinbefore in (4) (b) (i), (ii), (iii), (iv) or (v); (e) R₆₅ is chosenfrom hydrogen, C₁-C₆ alkyl or R_(a)said R_(a) being the same asdescribed hereinbefore in (d); (f) R₆₆ is chosen from hydrogen, C₁-C₆alkyl or R_(a), said R_(a) being the same as described hereinbefore in(d); or (g) R₆₅ and R₆₆ together form one of the following graphicformulae:

wherein J′ and K′ being independently chosen for each occurrence in eachformula from oxygen or —N(R₁₅)—, said R₁₅ being the same as describedhereinbefore in (2) (b), R₁₈ and R₁₉ each being the same as describedhereinbefore in (2) (d) (vi); and (h) B and B′ are each independentlychosen from the groups described hereinbefore in (2) (d); (14) aphotochromic material chosen from an indenonaphthopyran represented bythe following graphic formula XIV:

wherein, (a) R₇₄ and R₇₅ are each the same as R₆₂ and R₆₃ groupsdescribed hereinbefore in (13) (c); (b) each R₇₆ is independently chosenfor each occurrence from di(C₁-C₆)alkylamino, dicyclohexylamino,diphenylamino, piperidyl, morpholinyl, pyridyl, a group T, describedhereinbefore in (2) (d) (i) or group —C(O)W″ described hereinbefore in(11)(b) and q is the integer 0, 1, or 2; or when q is 2, and the R₇₆substituents are adjacent, each pair of substituents independently formsa substituted or unsubstituted fused carbocyclic or heterocyclic ringchosen from benzo, pyridino, pyrazino, pyrimidino, furano,dihydrofurano, 1,3-dioxolo, 1,4-dioxolo, 1,3-dioxino, 1,4-dioxino,thiopheno, benzofuro, benzothieno, indolo, or indeno, the substituentsof said fused carbocyclic or heterocyclic ring being chosen fromhalogen, C₁-C₆ alkyl, C₁-C₆ alkoxy, amino, mono- or di-substitutedamino, said amino substituents being chosen from C₁-C₆ alkyl, phenyl,benzyl or naphthyl; said first R₇₆ ring being fused to the o, p or qside and said second R₇₆ ring being fused to the g, h, or i side of theindenonaphthopyran; and (c) B and B′ are each independently chosen fromthe groups described hereinbefore in (2) (d); or (15) mixtures thereof.5. The photochromic article of claim 4 wherein photochromic material (b)is chosen from: (1) a photochromic material represented by graphicformula I wherein: (a) R₁ is chosen from C₁-C₈ alkyl, phen(C₁-C₄)alkyl,acrylyloxy(C₂-C₆)alkyl, methacrylyloxy(C₂-C₆)alkyl, carboxy(C₂-C₆)alkyl,tri(C₁-C₆)alkylsilyl, tri(C₁-C₆)alkylsilyloxy, tri(C₁-C₆)alkoxysilyl,tri(C₁-C₆)alkoxysilyloxy, di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyl,di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyloxy, di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silylor di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyloxy; (b) R₂ is chosen from C₁-C₅alkyl, C₁-C₅ alkoxy, C₁-C₈ alkoxycarbonyl, C₁-C₄ acyloxy, halo, C₁-C₄monohaloalkyl or C₁-C₄ polyhaloalkyl; said halo substituents beingchloro or fluoro, and q is 0, 1 or 2; (c) R₃ and R₄ are eachindependently chosen from C₁-C₅ alkyl, phenyl; or R₃ and R₄ takentogether form a group chosen from a cyclic ring of from 5 to 8 carbonatoms which includes the spiro carbon atom;; (d) R₅ is chosen from —CH₂Qand —C(O)W, wherein Q is halogen, hydroxy, C₁-C₆ alkoxy,tri(C₁-C₆)alkylsilyl, tri(C₁-C₆)alkylsilyloxy, tri(C₁-C₆)alkoxysilyl,tri(C₁-C₆)alkoxysilyloxy, di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyl,di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyloxy, di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyl,di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyloxy, or the group, —OCH(R₈)Z; W is thegroup, —OCH(R₈)Z, morpholino or piperidino; Z is —COOR₈, R₈ is C₁-C₆alkyl; or W is —OR₉ or —N(R₁₀)R₁₁, wherein R₉ is chosen from C₁-C₆ alkylor phenyl; and R₁₀ and R₁₁ are each independently chosen from hydrogen,C₁-C₆ alkyl, or R₁₀ and R₁₁ together with the nitrogen atom form aheterocyclic ring chosen from morpholino or piperidino; and each of saidhalogen or halo groups in this part (d) being fluoro or chloro; (e) eachR₆ and R₇ is independently chosen for each occurrence from aryl,mono(C₁-C₆)alkoxyaryl, di(C₁-C₆)alkylamino, piperidino, morpholino,C₁-C₆ alkoxy, or fluoro; and q is independently chosen for eachoccurrence form the integer 0, 1, or
 2. (2) a photochromic materialrepresented by graphic formula II wherein: (a) R₁₂ is hydrogen; (b) R₁₃is hydrogen or the group, —C(O)J, J being —OR₁₅ or —N(R₁₀)R₁₁, whereinR₁₅ is C₁-C₆ alkyl, phenyl(C₁-C₃)alkyl, or C₁-C₆ alkoxy(C₂-C₄)alkyl, R₁₀and R₁₁ are the same as described hereinbefore in (1) (d); (c) R₁₄ ishydrogen, C₁-C₆ alkyl, phenyl(C₁-C₃)alkyl, C₁-C₆ alkoxy(C₂-C₄)alkyl,C₅-C₇ cycloalkyl, or the group, —C(O)V; wherein V is C₁-C₆ alkyl, C₁-C₆alkoxy or C₁-C₆ alkylamino; and (d) B and B′ are each independentlychosen from: (i) an unsubstituted, mono-, di-, or tri-substituted phenylgroup; (ii) a mono-substituted heteroaromatic group chosen frombenzofuran-2-yl, benzothien-3-yl, dibenzofuranyl, or carbazoyl; each ofsaid phenyl and heteroaromatic substituents in (i) and (ii) beingindependently chosen from —C(O)U, wherein U being C₁-C₆ alkyl, C₁-C₆alkoxy, mono(C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, morpholino, orpiperidino; or amino, mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino,piperidino, morpholino or fluoro; (iii) an unsubstituted ormono-substituted phenothiazinyl, said substituents being C₁-C₆ alkyl orC₁-C₆ alkoxy; (iv) a monosubstituted phenyl, said phenyl having asubstituent located at the para position being —O—(CH₂)_(r)—, wherein rbeing chosen from the integer 3 or 6, said substituent being connectedto an aryl group which is a member of another photochromic material; (v)a group represented by one of the following graphic formulae:

wherein A being independently chosen in each formula from methylene oroxygen and D being independently chosen in each formula from oxygen orsubstituted nitrogen, provided that when D is substituted nitrogen, A ismethylene; said nitrogen substituents being C₁-C₆ alkyl; each R₂₀ beingindependently chosen for each occurrence in each formula from C₁-C₆alkyl or C₁-C₆ alkoxy; R₁₈ and R₁₉ each being independently chosen ineach formula from hydrogen or C₁-C₆ alkyl; and q being chosen from theinteger 0, 1 or 2; (vi) C₁-C₆ alkyl, C₃-C₆ cycloalkyl, or C₄-C₁₂bicycloalkyl; (vii) a group represented by the following graphicformula:

wherein L being hydrogen and M being an unsubstituted, mono-, ordi-substituted phenyl; each of said group substituents beingindependently chosen from C₁-C₄ alkoxy or fluoro; or (viii) B and B′taken together form fluoren-9-ylidene, mono-, or di-substitutedfluoren-9-ylidene or a saturated C₇-C₁₂ spiro-bicyclic hydrocarbonrings; each of said fluoren-9-ylidene substituents being fluoro; (3) aphotochromic material represented by graphic formula III wherein: (a)R₂₁ is the group, —C(O)W or CH₂Q, described hereinbefore in (1) (d); (b)R₂₂ and each R₂₃ are independently chosen for each occurrence fromhydroxy, NH₂ or N(R)H; wherein R is C₁-C₃ alkyl or phenyl and n ischosen from the integers 0, 1 or 2; (c) B and B′ are each independentlychosen from the groups described hereinbefore in (2) (d); (4) aphotochromic material represented by graphic formula IV wherein: (a) R₅is chosen from the groups described hereinbefore in (1) (d); (b) R₂₄ andR₂₅ are each chosen from hydrogen or an amino group defined hereinafter,provided that R₂₄ and R₂₅ are not both hydrogen; said amino group being:(i) —N(R₁₆)R₁₇, R₁₆ and R₁₇ each being independently chosen from C₁-C₈alkyl, aryl, or C₃-C₂₀ cycloalkyl; and said aryl group being phenyl ornaphthyl; (ii) a nitrogen containing ring represented by the followinggraphic formula:

wherein each Y being independently chosen for each occurrence from—CH₂—, ; X being —Y—, —O—, —S—, or —N(R₂₆)—; R₂₆ being C₁-C₆ alkyl; saidaryl group being phenyl or naphthyl, m being chosen from the integer 1,2 or 3 and p being chosen from the integer 0, 1, 2 or 3; provided thatwhen p is 0, X is Y; or (iii) a group represented by one of thefollowing graphic formulae:

wherein each R_(28,) R₂₉ and R₃₀ being chosen independently for eachoccurrence in each formula from hydrogen; R₂₇ being chosen independentlyfor each occurrence from C₁-C₆ alkyl, and q being chosen from theinteger 0, 1 or 2; (c) B and B′ are each independently chosen from thegroups described hereinbefore in (2) (d); (5) a photochromic materialrepresented by graphic formula V wherein: (a) R₃₁ is R₅ describedhereinbefore in (1) (d); (b) R₃₂ is hydrogen or C₁-C₆ alkyl; (c) eachR₃₃ is independently chosen for each occurrence from —N(R₁₀)R₁₁, whichwas described hereinbefore in (1) (d), C₁-C₆ alkyl, or —OR₃₄, whereinR₃₄ is C₁-C₆ alkyl, and q is the integer 0, 1, or 2; and (d) B and B′are each independently chosen from the groups described hereinbefore in(2) (d); (6) a photochromic material represented by graphic formula VIwherein: (a) R₃₅ and R₃₆ are each independently chosen for eachoccurrence from C₁-C₆ alkyl, C₁-C₆ alkoxy, fluoro, amino,mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, phenylamino, mono-ordi-(C₁-C₆)alkyl substituted phenylamino or mono- or di-(C₁-C₆)alkoxysubstituted phenylamino, and q is the integer 0, 1 or 2; (b) R₅ ischosen from the group described hereinbefore in (1) (d); and (c) B andB′ are each independently chosen from the groups described hereinbeforein (2) (d); (7) a photochromic material represented by graphic formulaVII wherein: (a) R₃₇ and R₃₈ together form an oxo group or R₃₇ and R₃₈each are independently chosen for each occurrence from hydrogen, C₁-C₆alkyl, C₃-C₇ cycloalkyl, phenyl or methacryloxy(C₁-C₆)alkyl; (b) R₃₉ ischosen from C₁-C₆ alkyl, C₁-C₆ alkoxy, fluoro, or morpholino, and q isthe integer 0, 1 or 2; (c) I is oxygen or —N(R₄₀)—, wherein R₄₀ is C₁-C₆alkyl, C₃-C₇ cycloalkyl or phenyl; (d) K is oxygen, —N(R₄₀)— or—C(R₄₁)(R₄₂)—, wherein R₄₁ and R₄₂ are each hydrogen or C₁-C₆ alkyl; and(e) B and B′ are each independently chosen from the groups describedhereinbefore in (2) (d); (8) a photochromic material represented bygraphic formula VIII wherein: (a) R₄₃ and R₄₄ together form an oxo groupor R₄₃ and R₄₄ are both hydrogen, C₁-C₆ alkyl, C₃-C₇ cycloalkyl orphenyl; (b) R₄₅ is hydrogen or C₁-C₆ alkyl; (c) R₄₆ is hydrogen or C₁-C₆alkyl, C₃-C₇ cycloalkyl; (d) each R₄₇ is C₁-C₆ alkyl, C₁-C₆ alkoxy orfluoro, and q is the integer 0, 1 or 2; and (e) B and B′ are eachindependently chosen from the groups described hereinbefore in (2) (d);(9) a photochromic material represented by graphic formulae IXA, IXB,IXC, IXD, IXE, IXF, IXG or IXH wherein: (a) R₄₃ and R₄₄ are the samegroups described hereinbefore in (8) (a); (b) each R₄₇ and q are thesame as described hereinbefore in (8) (d); and (c) B and B′ are eachindependently chosen from the groups described hereinbefore in (2) (d);(10) a photochromic material represented by graphic formulae XA or XBwherein: (a) A′ is chosen from: (i) an unsubstituted, mono- ordi-substituted heterocyclic ring; or (ii) an unsubstituted, mono- ordi-substituted indeno group, each of said heterocyclic ring and indenogroup substituents being C₁-C₄ alkyl, C₁-C₃ alkoxy, —N(R₁₀)R₁₁, whichwas described hereinbefore in (1) (d), benzo, mono- or di-substitutedbenzo fused to the indeno moiety, said benzo substituents being C₁-C₃alkyl, C₁-C₃ alkoxy or —N(R₁₀)R₁₁; (b) R₄₈ is chosen from: (i) —C(O)W′,W′ being —OR₉ or —N(R₁₀)R₁₁, which groups were described hereinbefore in(1) (d); or (ii) —C(R₅₁)₂X′, wherein X′ is —CN, halogen, hydroxy,benzoyloxy, C₁-C₄ alkoxy, C₂-C₄ acyloxy, amino, C₁-C₄ mono-alkylamino,C₁-C₄ dialkylamino, morpholino, piperidino, 1-indolinyl or pyrrolidyl,and R₅₁ is hydrogen, C₁-C₄ alkyl, phenyl or naphthyl; (c) R₄₉ ishydrogen, C₁-C₄ alkyl, the mono- or di-substituted aryl groups phenyl ornaphthyl, said aryl substituents being C₁-C₄ alkyl or C₁-C₄ alkoxy,chloro or fluoro; (d) each R₅₀ is fluoro, C₁-C₄ alkyl, C₁-C₄ alkoxy,phenyl, naphthyl, phenoxy, naphthoxy, or the group, —N(R₁₀)R₁₁,described hereinbefore in (1) (d), and q is selected from the integers0, 1 or 2 for the naphthopyran represented by graphic formula XA or p isselected from the integers 0, 1, 2 or 3 for the naphthopyran representedby graphic formula XB; and (e) B and B′ are each independently chosenfrom the groups described hereinbefore in (2) (d); (11) a photochromicmaterial represented by graphic formulae XIA or XIB wherein: (a) A″ isan unsubstituted, mono-substituted or di-substituted heterocyclic ringchosen from furo, thieno, benzothieno, benzofurano or indolo, the 2,3 or3,2 positions of said heterocyclic ring being fused to the p side ofsaid indenonaphthopyran, said heterocyclic ring substituents being C₁-C₆alkyl; (b) R₅₂ and R₅₃ together form an oxo group, a spiro heterocyclicgroup having 2 oxygen atoms and from 3 to 6 carbon atoms including thespirocarbon atom, or R₅₂ and R₅₃ are each hydrogen, hydroxy, C₁-C₆alkyl, C₃-C₇ cycloalkyl, phenyl or the group, —C(O)W″, wherein each W″is C₁-C₆ alkoxy, mono(C₁-C₆)alkylamino or di(C₁-C₆)alkylamino, or R₅₂and R₅₃ are each the group, —N(R₁₀)R₁₁, described hereinbefore in (1)(d), or —OR₅₄, wherein each R₅₄ is C₁-C₆ alkyl, phenyl(C₁-C₃)alkyl, thegroup, —CH(R₅₅)X″, wherein each R₅₅ is hydrogen or C₁-C₃ alkyl, each X″is —COOR₅₅, or each R₅₄ is the group, —C(O)Y′, wherein each Y′ is C₁-C₆alkyl; (c) each R₄₇ and q are the same as described hereinbefore in (8)(d); and (d) B and B′ are each independently chosen from the groupsdescribed hereinbefore in (2) (d); (12) a photochromic materialrepresented by graphic formulae XIIA or XIIB wherein: (a) A″ is the sameas the groups described hereinbefore in (11) (a); (b) R₅₆ is hydrogen orhydroxy and R₅₇ is the group, —CH(V′)₂, wherein V′ is —COOR₅₈, and eachR₅₈ is C₁-C₆ alkyl or phenyl(C₁-C₃)alkyl; or R₅₇ is the group,—CH(R₅₉)Y″, wherein R₅₉ is hydrogen and Y″ is —COOR₅₈, or —CH₂OR₆₀wherein R₅₉ is C₁-C₆ alkyl or di(C₁-C₆)alkylamino; and R₆₀ is C₁-C₆alkyl; or (c) R₅₆ and R₅₇ together form the group, ═C(R₅₉)W′″, whereinW′″ is —COOR₅₈; (d) each R₄₇ and q are the same as describedhereinbefore in (8) (d); and (e) B and B′ are each independently chosenfrom the groups described hereinbefore in (2) (d); (13) a photochromicmaterial represented by graphic formula XIII wherein: (a) R₆₁ isrepresented by: (i) —SR₆₇, R₆₇ being C₁-C₆ alkyl or aryl; (ii) an aminogroup described hereinbefore in (4) (b) (i), (ii) or (iii); (b) R₆₁′ isindependently chosen for each occurrence from C₁-C₆ alkyl or C₁-C₆alkoxy and q being the integer 1; (c) R₆₂ and R₆₃ are each independentlychosen from: (i) hydrogen, hydroxy, C₁-C₁₂ alkyl, C₃-C₁₂ alkylidene,C₃-C₇ cycloalkyl, or —C(O)W″, wherein W″ being the same group describedhereinbefore in (11) (b); (ii) an unsubstituted, mono- di- ortri-substituted group chosen from phenyl; each of said phenylsubstituents in (c) (ii) being chosen independently for each occurrencefrom chloro, fluoro, C₁-C₆ alkyl or C₁-C₆ alkoxy; (iii) amonosubstituted phenyl, described hereinbefore in (2) (d) (iv); (iv)—OR₆₇, R₆₇ being chosen from C₁-C₆ alkyl, phenyl(C₁-C₃)alkyl, C₁-C₆alkoxy(C₂-C₄)alkyl tri(C₁-C₆)alkylsilyl, tri(C₁-C₆)alkylsilyloxy,tri(C₁-C₆)alkoxysilyl, tri(C₁-C₆)alkoxysilyloxy, di(C₁-C₆)alkyl(C₁-C₆alkoxy)silyl, di(C₁-C₆)alkyl(C₁-C₆ alkoxy)silyloxy,di(C₁-C₆)alkoxy(C₁-C₆ alkyl)silyl or di(C₁-C₆)alkoxy(C₁-C₆alkyl)silyloxy; (v) —CH(Q′″)₂, Q′″ being chosen from —COOR₆₉ and R₆₉being C₁-C₆ alkyl; (vi) —CH(R₇₀)G″, R₇₀ being chosen from hydrogen,C₁-C₆ alkyl or an unsubstituted, mono- or di-substituted aryl group,phenyl or naphthyl, and G″ being chosen from —COOR₆₉, —COR₇₁ or—CH₂OR₇₂, wherein R₇₁ being chosen from hydrogen, C₁-C₆ alkyl, anunsubstituted, mono- or di-substituted aryl group, phenyl or naphthyl,amino, mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino, phenylamino, mono- ordi-(C₁-C₆)alkyl substituted phenylamino, mono- or di-(C₁-C₆)alkoxysubstituted phenylamino, diphenylamino, mono- or di(C₁-C₆)alkylsubstituted diphenylamino, mono- or di(C₁-C₆)alkoxy substituteddiphenylamino, morpholino or piperidino; R₇₂ being chosen from hydrogen,—C(O)R₆₉, C₁-C₆ alkyl, C₁-C₃ alkoxy(C₁-C₆)alkyl, phenyl(C₁-C₃)alkyl,mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl or an unsubstituted,mono- or di-substituted aryl group, phenyl or naphthyl, each of saidaryl group substituents being independently chosen from C₁-C₆ alkyl orC₁-C₆ alkoxy; or (vii) R₆₂ and R₆₃ together form an oxo group or asubstituted or unsubstituted spiro-carbocyclic ring containing 3 to 6carbon atoms or a substituted or unsubstituted spiro-heterocyclic groupcontaining 1 or 2 oxygen atoms and 3 to 6 carbon atoms including thespirocarbon atom, said spiro-carbocyclic ring and spiro-heterocyclicgroup being annellated with 0, 1 or 2 benzene rings, said substituentsbeing hydrogen or C₁-C₆ alkyl; (d) R₆₄ is chosen from hydrogen, C₁-C₆alkyl or the group R_(a) chosen from: (i) —OR₇₃, R₇₃ being chosen fromphenyl(C₁-C₃)alkyl, C₁-C₆ alkyl, mono(C₁-C₆)alkyl substitutedphenyl(C₁-C₃)alkyl, mono(C₁-C₆)alkoxy substituted phenyl(C₁-C₃)alkyl,C₁-C₆ alkoxy(C₂-C₄)alkyl, C₃-C₇ cycloalkyl, mono(C₁-C₄)alkyl substitutedC₃-C₇ cycloalkyl, C₁-C₆ chloroalkyl, C₁-C₆ fluoroalkyl, allyl or—CH(R₆₈)Q″; or (ii) an amino group described hereinbefore in (4) (b)(i), (ii) or (iii); (e) R₆₅ is chosen from hydrogen, C₁-C₆ alkyl orR_(a), said R_(a) being the same as described hereinbefore in (d); (f)R₆₆ is chosen from hydrogen, C₁-C₆ alkyl or R_(a), said R_(a) being thesame as described hereinbefore in (d); or (g) R₆₅ and R₆₆ together formone of the following graphic formulae:

wherein J′ and K′ being oxygen, said groups R₁₈ and R₁₉ each being thesame as described hereinbefore in (2) (d) (v); (h) B and B′ are eachindependently chosen from the groups described hereinbefore in (2) (d);(14) a photochromic material represented by graphic formula XIV wherein:(a) R₇₄ and R₇₅ are each the same as R₆₂ and R₆₃ groups describedhereinbefore in (13) (c); (b) each R₇₆ is independently chosen fromdi(C₁-C₆)alkylamino, dicyclohexylamino, diphenylamino, piperidyl,morpholinyl, pyridyl, halogen, or group —C(O)W″, the group C(O)W″ beingthe same group described hereinbefore in (11) (b); and q is the integer0, 1, or 2; or when q is 2, and the R₇₆ substituents are adjacent, eachpair of substituents independently forms a substituted or unsubstitutedfused carbocyclic or heterocyclic ring chosen from benzo, dihydrofurano,1,4-dioxolo, 1,3-dioxino, or benzofuro, the substituents of said fusedcarbocyclic or heterocyclic ring being chosen from the group consistingof C₁-C₆ alkyl or C₁-C₆ alkoxy; (c) B and B′ are each independentlychosen from the groups described hereinbefore in (2) (d); or (15)mixtures thereof.
 6. The photochromic article of claim 5 whereinphotochromic material (b) is chosen from: (1) a photochromic materialrepresented by graphic formula I chosen from: (a)1,3,3-trimethyl-spiro[indoline-2,5′-3H-fluorantheno[3,2-b][1,4]oxazine];(b) 1,3,3,4,5 (or1,3,3,5,6)-pentamethyl-spiro[indoline-2,5′-3H-fluorantheno[3,2-b][1,4]oxazine];(c) 1-propyl-3,3,4,5 (or3,3,5,6)-tetramethyl-spiro[indoline-2,5′-3H-fluorantheno[3,2-b][1,4]oxazine];or (d)1-methoxyethyl-3,3-dimethyl-spiro[indoline-2,5′-3H-fluorantheno[3,2-b][1,4]oxazine];(2) a photochromic material represented by graphic formula II chosenfrom: (a) 3,3-diphenyl-8-hydroxy-9-carbopropoxy-3H-naphtho[2,1-b]pyran;(b)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbopropoxy-3H-naphtho[2,1-b]pyran;(c)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(d)3-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-8-hydroxy-9-carbomethoxy-3H-naphtho{2,1-b]pyran;(e) 3,3-diphenyl-8-methoxy-9-carbophenoxy-3H-naphtho[2,1-b]pyran; (f)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-methoxy-9-carbophenoxy-3H-naphtho[2,1-b]pyran;(g)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(h)3-(2,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-8-acetoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(i) 3,3-diphenyl-7-methyl-8-methoxy-3H-naphtho [2,1-b]pyran; (j)3-(2-methoxy,4-acryloxyphenyl)-3-(4-methacryloxyphenyl)-8-benzyloxy-9-(carbo-1-indolinyl-3H-naphtho[2,1-b]pyran;(k)3-(2,4,6-trifluorophenyl)-3-(2,4,6-trimethoxy-1-naphthyl)-8-acetyl-9-carboniloyl-3H-naphtho[2,1-b]pyran;(l)3-(2-fluorophenyl)-3-(3-methoxy-2-thienyl)-7-h-pentyl-8-benzoyloxy-3H-naphtho[2,1-b]pyran;(m)3,3-spiroadamantylene-8-acetoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(n)3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(o)3-(4-methoxyphenyl)-3-(2-phenyl-1-methylvinyl)-8-acetoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(p)3-(4-methoxyphenyl)-3-(9-ethylcarbozol-2-yl)-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(q)3,3-spirofluoren-9-ylidene-8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran;or (r) 3,3-diphenyl-8-morpholino-9-carbomethoxy-3H-naphtho[2,1-b]pyran;(3) a photochromic material represented by graphic formula III chosenfrom: (a)2,2-(4-methoxyphenyl)-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;(b)2,2-(4-methoxyphenyl)-5-methoxycarbonyl-6-amino-2H-naphtho[1,2-b]pyran;(c)2,2-(4-methoxyphenyl)-5-methoxycarbonyl-6-propylamino-2H-naphtho[1,2-b]pyran;(d)2-(4-methoxyphenyl)-2-t-butyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran;(e)2-(4-methoxyphenyl)-2-phenyl-5-methoxycarbonyl-6-amino-2H-naphtho[1,2-b]pyran;(f)2,2-(4-methylphenyl)-5-methoxycarbonyl-6-methylamino-2H-naphtho[1,2-b]pyran;(g) 2,2-diphenyl-5-methoxycarbonyl-6-hydroxy-2H-naphtho[1,2-b]pyran; (h)2,2-(4-methoxyphenyl)-5-methoxycarbonyl-6-phenylamino-2H-naphtho[1,2-b]pyran;(i)2,2-(4-methoxyphenyl)-5-methoxycarbonyl-6-hydroxy,9-methoxy-2H-naphtho[1,2-b]pyran;(j) 2,2-diphenyl-5-methoxycarbonyl-6-phenylamino-2H-naphtho[1,2-b]pyran;(k)2,2-(3-trifluoromethylphenyl)-5-methoxycarbonyl,6-hydroxy-2H-naphtho[1,2-b]pyran;(1)2-(4-methoxyphenyl)-2-(2-methyl,2,3-dihydrobenzofur-5-yl),5-methoxycarbonyl-6-amino-2H-naphtho[1,2-b]pyran;or (m)2,2′-spiroadamantylene-5-methoxycarbonyl-6-methoxy-2H-naphtho[1,2-b]pyran;(4) a photochromic material represented by graphic formula IV chosenfrom: (a)2-phenyl-2-(4-morpholinophenyl)-5-carbomethoxy-9-dimethylamino-2H-naphtho[1,2-b]pyran;(b)2,2-di(4-methoxyphenyl)-5-methoxymethyl-9-morpholino-2H-naphtho[1,2-b]pyran;or (c)2-(4-methoxyphenyl)-2-(4-piperidinophenyl)-5-carbomethoxy-9-dimethylamino-2H-naphtho[1,2-b]pyran.(5) a photochromic material represented by graphic formula V chosenfrom: (a)3,3-diphenyl-12-methoxycarbonyl-11-methyl-3H-phenanthro[1,2-b]pyran; (b)2,2-diphenyl-5-methoxycarbonyl-6-methyl-2H-phenanthro[4,3-b]pyran; (c)2-(4-methoxyphenyl)-2-phenyl-5-methoxycarbonyl-6-methyl-2H-phenanthro[4,3-b]pyran;(d)3-(2-fluorophenyl)-3-(4-methoxyphenyl)-6-methoxy-12-methoxycarbonyl-3H-phenanthro[1,2-b]pyran;(e)spiro[3H-6-methoxy-12-methoxycarbonyl-phenanthro[1,2-b]pyran-3-9′-fluorene];(f)2,2-di(4-methoxyphenyl)-10-methoxy-5-methoxycarbonyl-6-methyl-2H-phenanthro[4,3-b]pyran;(g)3-(2,3-dihydrobenzofur-5-yl)-3-(4-methoxyphenyl)-6-methoxy-12-methoxycarbonyl-11-methyl-3H-phenanthro[1,2-b]pyran;(h)3,3-diphenyl-6-methoxy-12-methoxycarbonyl-11-phenyl-3H-phenanthro[1,2-b]pyran;(i)3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-6-methoxy-12-methoxycarbonyl-11-phenyl-3H-phenanthro[1,2-b]pyran;(j)3-(4-methoxyphenyl)-3-(2-methyl-2,3-dihydrobenzofur-5-yl)-6-methoxy-12-hydroxymethyl-11-phenyl-3H-phenanthro[1,2-b]pyran;or (k)2,2-diphenyl-5-N,N-dimethylaminocarbonyl-2H-phenanthro[4,3-b]pyran; (6)a photochromic material represented by graphic formula VI chosen from:(a)5,5-bis(4-methoxyphenyl)-8-ethoxycarbonyl-5H-fluorantheno[3,2-b]pyran;(b)5-(4-methoxyphenyl)-5-(4-morpholinophenyl)-8-ethoxycarbonyl-5H-fluorantheno[3,2-b]pyran;(c) 5,5-diphenyl-8-ethoxycarbonyl-5H-fluorantheno[3,2-b]pyran; (d)5,5-bis(4-methoxyphenyl)-8-methylol-5H-fluorantheno[3,2-b]pyran; or (e)5,5-bis(4-methoxyphenyl)-2-methoxy-8-methoxycarbonyl-5H-fluorantheno[3,2-b]pyran;(7) a photochromic material represented by graphic formula VII chosenfrom: (a)7,7-diphenyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran; (b)7,7-di(4-methoxyphenyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(c)7-(4-methoxyphenyl)-7-phenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(d)7,7-diphenyl-2-ethyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(e)7,7-diphenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(f)7,7-diphenyl-2-(2-methylpropyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[12-b]pyran;(g)2,7,7-triphenyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(h)7,7-diphenyl-2-(l-phenylethyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(i)3-methyl-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;(j)3-(2-ethoxycarbonylethyl)-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;(k)3-hexyl-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;(l)3-(2-methacryloyloxyethyl)-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;(m)2,2,7,7-tetraphenyl-4-oxo-2,3,4,7-tetrahydro-1H-pyrimidino[5′,4′:3,4]naphtho[1,2-b]pyran;(n)2,2,7,7-tetraphenyl-4-oxo-2,3,4,7-tetrahydro-1H-[1,3]oxazino[5′,4′:3,4]naphtho[1,2-b]pyran;(o)7,7-diphenyl-1,2,4,7-tetrahydro-2,2-dimethylpyrano[3′,4′:3,4]naphtho[1,2-b]pyran;(p)7-phenyl-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(q)7-(2-fluorophenyl)-7-(3-methyl-4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(r)7-(4-methoxyphenyl)-7-(2,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(s)7-(4-morpholino-2-fluorophenyl)-7-(4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(t)7-(2-fluoro-4-methoxyphenyl)-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;or (u)7-(4-morpholino-2-fluorophenyl)-7-(3,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(8) a photochromic material represented by graphic formula VIII chosenfrom: (a)7,7-diphenyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran; (b)7,7-di(4-methoxyphenyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(c)7-(4-methoxyphenyl)-7-phenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(d)7,7-diphenyl-2-ethyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(e)7,7-diphenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(f)7,7-diphenyl-2-(2-methylpropyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(g)2,7,7-triphenyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(h)7,7-diphenyl-2-(1-phenylethyl)-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(i)3-methyl-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;(j)3-(2-ethoxycarbonylethyl)-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;(k)3-hexyl-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;(1)3-(2-methacryloyloxyethyl)-7,7-diphenyl-2,4-dioxo-2,3,4,7-tetrahydro[1,3]oxazino[5′,6′:3,4]naphtho[1,2-b]pyran;(m)2,2,7,7-tetraphenyl-4-oxo-2,3,4,7-tetrahydro-1H-pyrimidino[5′,4′:3,4]naphtho[1,2-b]pyran;(n)2,2,7,7-tetraphenyl-4-oxo-2,3,4,7-tetrahydro-1H-[1,3]oxazino[5′,4′:3,4]naphtho[1,2-b]pyran;(o)7,7-diphenyl-1,2,4,7-tetrahydro-2,2-dimethylpyrano[3′,4′:3,4]naphtho[1,2-b]pyran;or (p)2-(4-methoxyphenyl)-2-(2,4-dimethoxy-phenyl)-7-diphenylmethyl-10-methyl-5-oxo-2H-5H-pyrano[3′,4′:3,4]naphtho[1,2-b]pyran;(9) a photochromic material represented by graphic formula IXA, IXB, IXCor IXD chosen from: (a)2,2-bis(4-methoxyphenyl)-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;(b)6,6-bis(4-methoxyphenyl)-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(c)6,6-bis(4-methoxyphenyl)-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(d)2-(4-methoxyphenyl)-2-(4-morpholinophenyl)-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;(e)6-(4-methoxyphenyl)-6-(4-morpholinophenyl)-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(f)10,10-dimethyl-6-(4-methoxyphenyl)-6-(4-morpholinophenyl)-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(g)2-(4-morpholinophenyl)-2-phenyl-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;(h)6-(4-morpholinophenyl)-6-phenyl-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(i)2,2-bis(4-methoxyphenyl)-12,13-dimethoxy-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;(j)6,6-bis(4-methoxyphenyl)-12,13-dimethoxy-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran; (k)6-(4-methoxyphenyl)-6-phenyl-12,13-dimethoxy-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(1)2-(4-methoxyphenyl)-2-phenyl-12,13-dimethoxy-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;(m)6,6-(4-methoxyphenyl)-6-phenyl-12,13-dimethoxy-10,10-dimethyl-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(n)2,2-bis(4-methoxphenyl)-12-methoxy-10-oxo-2,10-dihydro[2]benzopyrano[4′,3′:3,4]naphtho(2,1-b)pyran;(o)6-bis(4-methoxyphenyl)-12-methoxy-10-oxo-6,10-dihydro[2]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;(p)6,6-diphenyl-9-oxo-6,9-dihydro[1]benzopyrano[3′,4′:3,4]naphtho(1,2-b)pyran;or (q)3,3-diphenyl-8-oxo-3,8-dihydro[2]benzopyrano[3′,4′:5,6]naphtho(2,1-b)pyran;(10) a photochromic material represented by graphic formula XA or XBchosen from: (a)2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-methyl-2H-benzofuro[2′,3′:7,8]naphtho[1,2-b]pyran;(b)2-(4-methoxyphenyl)-2-(4-propoxyphenyl)-5-methoxycarbonyl-6-methyl-2H-benzofuro[2′,3′:7,8]naphtho[1,2-b]pyran;(c)2,2′-spiroadamantylene-5-methoxycarbonyl-6-methyl-2H-benzofuro[2′,3′:7,8]naphtho[1,2-b]pyran;(d)3,3-bis(4-methoxyphenyl)-10-methoxy-3H-naphtho[2″,1″:4′,5′]furo[2′,3′:3,4]naphtho[1,2-b]pyran;(e)3,3-bis(4-methoxyphenyl)-3H-naphtho[1″,2″:4′,5′]furo[3′,2′:3,4]naphtho[1,2-b]pyran;(f)3,3′-spiroadamantylene-3H-naphtho[1″,2″:4′,5′]furo[3′,2′:3,4]naphtho[1,2-b]pyran;(g)2,2-bis(4-methoxyphenyl)-5-methoxycarbonyl-6-methyl-2H-indeno[3′,2′:7:8]naphtho[1,2-b]pyran;(h)3,3-di(4-methoxyphenyl)-6,11-dimethoxy-13-butyl-13-ethoxy-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;or (i)3,3-di(4-methoxyphenyl)-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;(11) a photochromic material represented by graphic formula XIA or XIBchosen from: (a)3,3-di(4-methoxyphenyl)-16-hydroxy-16-ethyl-16H-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(b)3,3-di(4-methoxyphenyl)-16-hydroxy-[16H]-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran;or (c)3,3-di(4-methoxyphenyl)-16-hydroxy-16-ethyl-16H-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran;(12) a photochromic material represented by graphic formula XIIA or XIIBchosen from: (a)3,3-di(4-methoxyphenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(b)3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro[2′,3′:7,8]indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(c)3-phenyl-3-(4-methoxyphenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran; or (d)3-phenyl-3-(4-morpholinophenyl)-16-(ethoxycarbonyl)methyl-16-hydroxy-3,16-di[H]-benzofuro[2″,3″:6′,7′]indeno[3′,2′:4,3]naphtho[1,2-b]pyran; (13) a photochromic material representedby graphic formula XIII chosen from: (a)3,3-di(4-methoxyphenyl)-ll-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(b)3-phenyl-3-(4-morpholinophenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho-[1,2-b]pyran;(c)3,3-di(4-(2-methoxyethoxyphenyl))-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(d)3,3-di(4-methoxyphenyl)-11-morpholino-13-hydroxy-13-ethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(e)3,3-di(4-methoxyphenyl)-10-methoxy-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(f)3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-10-methoxy-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;(g)3-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran;or (h)3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′:3,4]naphtho[1,2-b]pyran; (i)3-(4-methoxyphenyl)-3-phenyl-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;or (j)3,3-di(2-methoxyethoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;(14) a photochromic material represented by graphic formula XTV chosenfrom: (a) 3,3,9-triphenyl-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(b)3,3-di(4-methoxyphenyl)-9-phenyl-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(c)3-(4-methoxyphenyl)-3,9-diphenyl-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(d)3-(4-morpholinophenyl)-3,9-diphenyl-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(e)3,3-di(4-methoxyphenyl)-9-(3-methoxyphenyl)-11-methoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(f)3-(4-methoxyphenyl)-3-phenyl-9-(3-methoxyphenyl)-11-methoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(g)3-(4-methoxyphenyl)-3-phenyl-9-methyl-11-methoxy-9-(3-methoxyphenyl)-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(h)3,3-di(4-methoxyphenyl)-9-methyl-11-methoxy-9-(3-methoxyphenyl)-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(i)3,3-di(4-methoxyphenyl)-9-methyl-11-methoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(j)3,3-di(4-methoxyphenyl)-9,9-dimethyl-11-methoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(k)3-(4-methoxyphenyl)-3-phenyl-9,9-dimethyl-11-methoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(l)3,3-di(4-methoxyphenyl)-9,9-dimethyl-7,11-dimethoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(m)3-(4-methoxyphenyl)-3-phenyl-9,9-dimethyl-7,11-dimethoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(n)3-(4-morpholinophenyl)-3-phenyl-9,9-dimethyl-7,11-dimethoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(o)3,3-di(4-methoxyphenyl)-9-methyl-11,13-dimethoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(p)3-(4-methoxyphenyl)-3-phenyl-9-methyl-11,13-dimethoxy-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;(q)3-(4-methoxyphenyl)-3-phenyl-9,9-dimethyl-3H-9H-benzo[4″,5″]indeno[3′,2′:3,4]naphtho[1,2-b]pyran;or (r)3,3-di(4-methoxyphenyl-9,9-dimethyl-11-fluoro-3H-9H-indeno[3′,2′:3,4]naphtho[1,2-b]pyran;or (15) mixtures thereof.
 7. The photochromic article of claim 6 whereinphotochromic material (b) is chosen from: (a)7,7-diphenyl-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(b)7-phenyl-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(c)3,3-di(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;(d)3-(4-morpholinophenyl)-3-phenyl-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;(e)7-(2-fluorophenyl)-7-(3-methyl-4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(f)3-(4-methoxyphenyl)-3-phenyl-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;(g)2-(4-methoxyphenyl)-2-(2,4-dimethoxyphenyl)-7-diphenylmethyl-10-methyl-5-oxo-2H-5H-pyrano[3′,4′:3,4]naphtho[1,2-b]pyran;(h)7-(4-methoxyphenyl)-7-(2,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(i)7-(4-morpholino-2-fluorophenyl)-7-(4-methoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(j)7-(2-fluoro-4-methoxyphenyl)-7-(4-morpholinophenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(k)7-(4-morpholino-2-fluorophenyl)-7-(3,4-dimethoxyphenyl)-2-pentyl-4-oxo-4H-7H-[1,3]dioxino[5′,4′:3,4]naphtho[1,2-b]pyran;(l)3-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;(m)3,3-di(2-methoxyethoxyphenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;(n)3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-11-morpholino-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;(o)3,3-di(4-methoxyphenyl)-6,11-dimethoxy-13-butyl-13-ethoxy-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;(p)3,3-di(4-methoxyphenyl)-10,11-dimethoxy-13,13-dimethyl-13H-3H-indeno[2′,3′,3,4]naphtho[1,2-b]pyran;or (q) mixtures thereof.
 8. The photochromic article of claim 1 furthercomprising at least one fixed tint dye.
 9. The photochromic article ofclaim 1 wherein said photochromic article is adapted to exhibit aneutral activated color.
 10. The photochromic article of claim 1 furthercomprising at least one other photochromic material (c) that isdifferent from photochromic material (b).
 11. The photochromic articleof claim 10 wherein photochromic material (c) is an organic photochromicmaterial, inorganic photochromic material or a mixture thereof.
 12. Thephotochromic article of claim 11 wherein photochromic material (c) is anorganic photochromic material and is chosen from naphthopyrans,benzopyrans, phenanthropyrans, indenonaphthopyrans, oxazines,metal-dithiozonates, fulgides, fulgimides, spiro(indoline)pyrans ormixtures thereof.
 13. The photochromic article of claim 11 whereinphotochromic material (c) is an inorganic photochromic material and ischosen from silver halide, cadmium halide, copper halide europium (II),cerium(III) or mixtures thereof.
 14. The photochromic article of claim 1further comprising an at least partial coating of an at least partiallyabrasion resistant coating applied to at least one surface of thesubstrate.
 15. The photochromic article of claim 14 further comprisingan at least partial coating of an at least partially antireflectivecoating applied to the at least partial coating of an at least partiallyabrasion resistant coating.
 16. The photochromic article of claim 1wherein the substrate comprises at least one photochromic material (b).17. The photochromic article of claim 16 wherein the substrate furthercomprises at least one photochromic material (c) that is different fromphotochromic material (b).
 18. The photochromic article of claim 1further comprising an at least partial coating of an at least partiallycured polymeric coating applied to at least one surface of thesubstrate.
 19. The photochromic article of claim 18 wherein the at leastpartially cured polymeric coating comprises photochromic material (b).20. The photochromic article of claim 19 wherein the at least partiallycured polymeric coating further comprises at least one otherphotochromic material (c) that is different from photochromic material(b).
 21. The photochromic article of claim 18 wherein the at leastpartially cured polymeric coating is a polymeric coating ofthermoplastic or thermosetting materials.
 22. The photochromic articleof claim 21 wherein the at least partially cured polymeric coating is apolymeric coating of thermosetting materials chosen from polyurethanes,aminoplast resins, poly(meth)acrylates, polyanhydrides, polyacrylamides,epoxy resins or polysilanes.
 23. The photochromic article of claim 18further comprising an at least partial coating of primer interposedbetween the at least partially cured polymeric coating and thesubstrate.
 24. The photochromic article of claim 23 further comprisingan at least partial coating of an at least partially abrasion resistantcoating applied to the surface of the at least partially cured polymericcoating.
 25. The photochromic article of claim 24 further comprising anat least partial coating of an at least partially antireflective coatingapplied to the at least partial coating of an at least partiallyabrasion resistant coating applied to the surface of the at leastpartially cured polymeric coating.
 26. The photochromic article of claim1 wherein the substrate is chosen from paper, glass, ceramic, wood,masonry, textile, metal or organic polymeric material.
 27. Thephotochromic article of claim 26 wherein the substrate is organicpolymeric material and said organic polymeric material is chosen frompoly(C₁-C₁₂ alkyl methacrylates), poly(oxyalkylene dimethacrylates),poly(alkoxylated phenol methacrylates), cellulose acetate, cellulosetriacetate, cellulose acetate propionate, cellulose acetate butyrate,poly(vinyl acetate), poly(vinyl alcohol), poly(vinyl chloride),poly(vinylidene chloride), thermoplastic polycarbonates, polyesters,polyurethanes, poly(ethylene terephthalate), polystyrene, poly(alphamethylstyrene), copoly(styrene-methylmethacrylate),copoly(styrene-acrylonitrile), polyvinylbutyral or is polymerized frommonomers chosen from bis(allyl carbonate) monomers, polyfunctionalacrylate monomers, polyfunctional methacrylate monomers, diethyleneglycol dimethacrylate monomers, diisopropenyl benzene monomers,ethoxylated bisphenol A dimethacrylate monomers, ethylene glycolbismethacrylate monomers, poly(ethylene glycol) bismethacrylatemonomers, ethoxylated phenol bis methacrylate monomers, alkoxylatedpolyhydric alcohol polyacrylate monomers, styrene monomers, urethaneacrylate monomers, glycidyl acrylate monomers, glycidyl methacrylatemonomers, diallylidene pentaerythritol monomers or mixtures thereof. 28.The photochromic article of claim 27 wherein the substrate is an organicpolymeric material and said organic polymeric material is an opticalelement.
 29. The photochromic article of claim 28 wherein the substrateis an optical element and said optical element is an ophthalmic lens.30. The photochromic article of claim 1 further comprising a superstrateconnected to at least a portion of the substrate, said superstratecomprising at least one organic polymeric material.
 31. The photochromicarticle of claim 30 wherein said superstrate comprises photochromicmaterial (b).
 32. The photochromic article of claim 31 wherein saidsuperstrate further comprises at least one other photochromic material(c) that is different from photochromic material (b).
 33. Thephotochromic article of claim 30 wherein the superstrate is adheringlybonded to at least a portion of the substrate.
 34. The photochromicarticle of claim 30 wherein the superstrate is an organic polymericmaterial chosen from thermosetting or thermoplastic materials.
 35. Thephotochromic article of claim 34 wherein the superstrate is athermoplastic material and is polyurethane.
 36. The photochromic articleof claim 30 further comprising an at least partially abrasion resistantfilm superposed on at least a portion of the superstrate.
 37. Thephotochromic article of claim 36 wherein the at least partially abrasionresistant film is an organic polymeric material chosen fromthermoplastic and thermosetting materials.
 38. The photochromic articleof claim 37 wherein the at least partially abrasion resistant film is athermoplastic material and is polycarbonate.
 39. The photochromicarticle of claim 36 further comprising an at least partial coating of anat least partially antireflective coating applied to the at leastpartially abrasion resistant film superposed on at least a portion ofthe superstrate.
 40. A photochromic article comprising: a) a substrate;and b) at least one photochromic material adapted to change from anunactivated form to an activated form by exposure to radiationsubstantially in the wavelength range from 380 to 410 nanometers whenmeasured over a range of from 380 to 700 nanometers, said photochromicarticle being adapted to retain at least 12 percent of the delta ODmeasured in the Outdoor Test when tested in the Behind the WindshieldTest; said photochromic article being substantially free of ultravioletradiation absorbing materials adapted to substantially inhibit theactivation of said photochromic material by radiation below 380nanometers.
 41. A photochromic article comprising: a) a substrate; andb) at least one photochromic material adapted to change from anunactivated form to an activated form by radiation substantially in awavelength range from 380 to 410 nanometers when measured over a rangeof from 380 to 700 nanometers, said photochromic article being adaptedto exhibit an unactivated state luminous transmittance of greater than70 percent at 23° C., an activated state luminous transmittance atsaturation less than 30 percent when activated at 23° C. by simulatedsunlight from a xenon arc lamp set at 6.7 Watts/meter² UVA and 50,000lumens/meter², and an activated state luminous transmittance atsaturation less than 60 percent when activated at 28° C. by simulatedsunlight from a xenon arc lamp through an UV blocking transparencyrendering an irradiance integrated between 380 and 420 nanometers of0.75 Watts/meter² and 1,700 lumens/meter².
 42. The photochromic articleof claim 41 wherein the photochromic article is adapted to exhibit anunactivated state luminous transmittance of greater than 80 percent at23° C., an activated state luminous transmittance at saturation lessthan 30 percent when activated at 23° C. by simulated sunlight from axenon arc lamp set at 6.7 Watts/meter² UVA and 50,000 lumens/meter², andan activated state luminous transmittance at saturation less than 40percent when activated at 28° C. by simulated sunlight from a xenon arclamp through an UV blocking transparency rendering an irradianceintegrated between 380 and 420 nanometers of 0.75 Watts/meter² and 1,700lumens/meter².
 43. The photochromic article of claim 41 wherein the UVblocking transparency is a vehicular windshield.
 44. The photochromicarticle of claim 41 further comprising at least one fixed tint dye. 45.The photochromic article of claim 41 wherein said photochromic articleis adapted to exhibit a neutral activated color.
 46. The photochromicarticle of claim 41 wherein photochromic material (b) is chosen from:(a) a single photochromic compound; (b) a mixture of photochromiccompounds; (c) a material comprising at least one photochromic compound;(d) a material to which at least one photochromic compound is chemicallybonded; (e) material (c) or (d) further comprising a coating tosubstantially prevent contact of the at least one photochromic compoundwith external materials; (f) a photochromic polymer; or (g) mixturesthereof.
 47. The photochromic article of claim 41 further comprising atleast one other photochromic material (c) that is different fromphotochromic material (b).
 48. The photochromic article of claim 47wherein photochromic material (c) is chosen from: (a) a singlephotochromic compound; (b) a mixture of photochromic compounds; (c) amaterial comprising at least one photochromic compound; (d) a materialto which at least one photochromic compound is chemically bonded; (e)material (c) or (d) further comprising a coating to substantiallyprevent contact of the at least one photochromic compound with externalmaterials; (f) a photochromic polymer; or (g) mixtures thereof.
 49. Thephotochromic article of claim 41 further comprising an at least partialcoating of an at least partially abrasion resistant coating.
 50. Thephotochromic article of claim 49 further comprising an at least partialcoating of an at least partially antireflective coating.
 51. Thephotochromic article of claim 41 wherein the substrate comprises atleast one photochromic material (b).
 52. The photochromic article ofclaim 51 wherein the substrate further comprises at least onephotochromic material (c) that is different from photochromic material(b).
 53. The photochromic article of claim 41 further comprising an atleast partial coating of an at least partially cured polymeric coatingapplied to at least one surface of the substrate.
 54. The photochromicarticle of claim 53 wherein the at least partially cured polymericcoating comprises photochromic material (b).
 55. The photochromicarticle of claim 54 wherein the at least partially cured polymericcoating further comprises at least one other photochromic material (c)that is different from photochromic material (b).
 56. The photochromicarticle of claim 53 wherein the at least partially cured polymericcoating is a polymeric coating of thermoplastic or thermosettingmaterials.
 57. The photochromic article of claim 56 wherein the at leastpartially cured polymeric coating is a polymeric coating ofthermosetting materials chosen from polyurethanes, aminoplast resins,poly(meth)acrylates, polyanhydrides, polyacrylamides, epoxy resins orpolysilanes.
 58. The photochromic article of claim 53 further comprisingan at least partial coating of primer interposed between the at leastpartially cured polymeric coating and the substrate.
 59. Thephotochromic article of claim 58 further comprising an at least partialcoating of an at least partially abrasion resistant coating applied tothe surface of the at least partially cured polymeric coating.
 60. Thephotochromic article of claim 59 further comprising an at least partialcoating of an at least partially antireflective coating.
 61. Thephotochromic article of claim 41 wherein the substrate is chosen frompaper, glass, ceramic, wood, masonry, textile, metal or organicpolymeric material.
 62. The photochromic article of claim 61 wherein thesubstrate is organic polymeric material and said organic polymericmaterial is chosen from poly(C₁-C₁₂ alkyl methacrylates),poly(oxyalkylene dimethacrylates), poly(alkoxylated phenolmethacrylates), cellulose acetate, cellulose triacetate, celluloseacetate propionate, cellulose acetate butyrate, poly(vinyl acetate),poly(vinyl alcohol), poly(vinyl chloride), poly(vinylidene chloride),thermoplastic polycarbonates, polyesters, polyurethanes, poly(ethyleneterephthalate), polystyrene, poly(alpha methylstyrene),copoly(styrene-methylmethacrylate), copoly(styrene-acrylonitrile),polyvinylbutyral or is polymerized from monomers chosen from bis(allylcarbonate) monomers, polyfunctional acrylate monomers, polyfunctionalmethacrylate monomers, diethylene glycol dimethacrylate monomers,diisopropenyl benzene monomers, ethoxylated bisphenol A dimethacrylatemonomers, ethylene glycol bismethacrylate monomers, poly(ethyleneglycol) bismethacrylate monomers, ethoxylated phenol bis methacrylatemonomers, alkoxylated polyhydric alcohol polyacrylate monomers, styrenemonomers, urethane acrylate monomers, glycidyl acrylate monomers,glycidyl methacrylate monomers, diallylidene pentaerythritol monomers ormixtures thereof.
 63. The photochromic article of claim 62 wherein thesubstrate is an organic polymeric material and said organic polymericmaterial is an optical element.
 64. The photochromic article of claim 63wherein the substrate is an optical element and said optical element isan ophthalmic lens.
 65. The photochromic article of claim 41 furthercomprising a superstrate connected to at least a portion of thesubstrate, said superstrate comprising at least one organic polymericmaterial.
 66. The photochromic article of claim 65 wherein thesuperstrate comprises photochromic material (b).
 67. The photochromicarticle of claim 66 wherein the superstrate further comprises at leastone other photochromic material (c) that is different from photochromicmaterial (b).
 68. The photochromic article of claim 65 wherein thesuperstrate is adheringly bonded to at least a portion of the substrate.69. The photochromic article of claim 65 wherein the superstrate is anorganic polymeric material chosen from thermosetting or thermoplasticmaterials.
 70. The photochromic article of claim 69 wherein thesuperstrate is a thermoplastic material and is polyurethane.
 71. Thephotochromic article of claim 65 further comprising an at leastpartially abrasion resistant film superposed on at least a portion ofthe superstrate.
 72. The photochromic article of claim 71 wherein the atleast partially abrasion resistant film is an organic polymeric materialchosen from thermoplastic and thermosetting materials.
 73. Thephotochromic article of claim 72 wherein the at least partially abrasionresistant film is a thermoplastic material and is polycarbonate.
 74. Thephotochromic article of claim 73 further comprising an at least partialcoating of an at least partially antireflective coating.
 75. Aphotochromic article comprising: a) a substrate; and b) at least onephotochromic material adapted to change from an unactivated form to anactivated form by radiation substantially in a wavelength range from 380to 410 nanometers when measured over a range of from 380 to 700nanometers, said photochromic article being adapted to exhibit anunactivated state luminous transmittance of greater than 70 percent at23° C., an activated state luminous transmittance at saturation lessthan 30 percent when activated at 23° C. by simulated sunlight from axenon arc lamp set at 6.7 Watts/meter² UVA and 50,000 lumens/meter², andan activated state luminous transmittance at saturation less than 60percent when activated at 28° C. by simulated sunlight from a xenon arclamp through an UV blocking transparency rendering an irradianceintegrated between 380 and 420 nanometers of 0.75 Watts/meter² and 1,700lumens/meter²; said photochromic article being substantially free ofultraviolet radiation absorbing materials adapted to substantiallyinhibit the activation of said photochromic material by radiation below380 nanometers.
 76. A method for producing a photochromic articleadapted to retain at least 12 percent of the delta OD measured in theOutdoor Test when tested in the Behind the Windshield Test comprising:a) obtaining a substrate; b) obtaining a photochromic material adaptedto change from an unactivated form to an activated form by exposure toradiation substantially in the wavelength range from 380 to 410nanometers when measured over a range of from 380 to 700 nanometers; c)introducing said photochromic material together with said substrate by amethod chosen from: i) introducing photochromic material (b) with thestarting materials used to form said substrate; ii) at least partiallyimbibing photochromic material (b) into at least one surface of saidsubstrate; iii) applying at least a partial coating of a polymericcoating composition comprising photochromic material (b) to at least onesurface of said substrate; iv) at least partially connecting asuperstrate comprising photochromic material (b) to at least one surfaceof said substrate; or v) combinations of i), ii), ii) or iv).
 77. Themethod of claim 76 further comprising adding a photochromic material (c)that is different from photochromic material (b), in (c) (i), (ii),(iii), (iv) or (v).
 78. The method of claim 76 further comprising addinga fixed tint dye in (c) (i), (ii), (iii), (iv) or (v).
 79. A method forproducing a photochromic article adapted to retain at least 12 percentof the delta OD measured in the Outdoor Test when tested in the Behindthe Windshield Test, said photochromic article being substantially freeof ultraviolet radiation absorbing materials adapted to substantiallyinhibit the activation of said photochromic material by radiation below380 nanometers comprising: a) obtaining a substrate; b) obtaining aphotochromic material adapted to change from an unactivated form to anactivated form by exposure to radiation substantially in the wavelengthrange from 380 to 410 nanometers when measured over a range of from 380to 700 nanometers; c) introducing said photochromic material togetherwith said substrate by a method chosen from: i) introducing photochromicmaterial (b) with the starting materials used to form said substrate;ii) at least partially imbibing photochromic material (b) into at leastone surface of said substrate; iii) applying at least a partial coatingof a polymeric coating composition comprising photochromic material (b)to at least one surface of said substrate; iv) at least partiallyconnecting a superstrate comprising photochromic material (b) to atleast one surface of said substrate; or v) a combination of i), ii), ii)or iv).
 80. A method for producing a photochromic article adapted toexhibit an unactivated state luminous transmittance of greater than 70percent at 23° C., an activated state luminous transmittance atsaturation less than 30 percent when activated at 23° C. by simulatedsunlight from a xenon arc lamp set at 6.7 Watts/meter² UVA and 50,000lumens/meter², and an activated state luminous transmittance atsaturation less than 60 percent when activated at 28° C. by simulatedsunlight from a xenon arc lamp through an UV blocking transparencyrendering an irradiance integrated between 380 and 420 nanometers of0.75 Watts/meter² and 1,700 lumens/meter², said photochromic articlebeing substantially free of ultraviolet radiation absorbing materialsadapted to substantially inhibit the activation of said photochromicmaterial by radiation below 380 nanometers; said method comprising: a)obtaining a substrate; b) obtaining a photochromic material adapted tochange from an unactivated form to an activated form by exposure toradiation substantially in the wavelength range from 380 to 410nanometers when measured over a range of from 380 to 700 nanometers; c)introducing said photochromic material with said substrate by a methodchosen from: i) introducing photochromic material (b) with the startingmaterials used to form said substrate; ii) at least partially imbibingphotochromic material (b) into at least one surface of said substrate;iii) applying at least a partial coating of a polymeric coatingcomposition comprising photochromic material (b) to at least one surfaceof said substrate; iv) at least partially connecting a superstratecomprising photochromic material (b) to at least one surface of saidsubstrate; or v) a combination of i), ii), ii) or iv).
 81. A method forproducing a photochromic article adapted to exhibit an unactivated stateluminous transmittance of greater than 70 percent at 23° C., anactivated state luminous transmittance at saturation less than 30percent when activated at 23° C. by simulated sunlight from a xenon arclamp set at 6.7 Watts/meter² UVA and 50,000 lumens/meter², and anactivated state luminous transmittance at saturation less than 60percent when activated at 28° C. by simulated sunlight from a xenon arclamp through an UV blocking transparency rendering an irradianceintegrated between 380 and 420 nanometers of 0.75 Watts/meter² and 1,700lumens/meter², comprising: a) obtaining a substrate; b) obtaining aphotochromic material adapted to change from an unactivated form to anactivated form by exposure to radiation substantially in the wavelengthrange from 380 to 410 nanometers when measured over a range of from 380to 700 nanometers; c) introducing said photochromic material togetherwith said substrate by a method chosen from: i) adding photochromicmaterial (b) with the starting materials used to form said substrate;ii) at least partially imbibing photochromic material (b) into at leastone surface of said substrate; iii) applying at least a partial coatingof a polymeric coating composition comprising photochromic material (b)to at least one surface of said substrate; iv) at least partiallyconnecting a superstrate comprising photochromic material (b) to atleast one surface of said substrate; or v) a combination of i), ii), ii)or iv).